CN102718694A - 3-cyan substituted indole compound and synthetic method thereof - Google Patents

3-cyan substituted indole compound and synthetic method thereof Download PDF

Info

Publication number
CN102718694A
CN102718694A CN2012102133390A CN201210213339A CN102718694A CN 102718694 A CN102718694 A CN 102718694A CN 2012102133390 A CN2012102133390 A CN 2012102133390A CN 201210213339 A CN201210213339 A CN 201210213339A CN 102718694 A CN102718694 A CN 102718694A
Authority
CN
China
Prior art keywords
indoles
reaction
cyanic acid
substituted indole
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN2012102133390A
Other languages
Chinese (zh)
Other versions
CN102718694B (en
Inventor
许斌
徐曙光
常广军
刘文婷
刘秉新
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Shanghai for Science and Technology
Original Assignee
University of Shanghai for Science and Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of Shanghai for Science and Technology filed Critical University of Shanghai for Science and Technology
Priority to CN201210213339.0A priority Critical patent/CN102718694B/en
Publication of CN102718694A publication Critical patent/CN102718694A/en
Application granted granted Critical
Publication of CN102718694B publication Critical patent/CN102718694B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Abstract

The invention relates to a 3-cyan substituted indole compound and a synthetic method thereof. The constitutional formula of the compound is that R1 is a methoxy group, and R2 is phenyl (Ph), benzyl (Bn), allyl or n-butyl. According to the synthetic method of the 3-cyan substituted indole compound, raw materials are easy to obtain, novel tertiary butyl isonitrile is firstly used as a source of cyan, and high toxic metal cyanide is avoided to be used. During the reaction, conventional reaction solvents are used, the operation is simple, the operation condition is moderate, the reaction is environment-friendly, the top yield can reach 74%, and the 3-cyan substituted indole compound has a good application prospect in industrial production.

Description

3-cyanic acid substituted indole compound and compound method thereof
Technical field
The present invention relates to a kind of cyanic acid substituted indole compound and preparation method thereof, mainly is 3-cyanic acid substituted indole compound and preparation method thereof.
Background technology
Organic cyanide is one type of very important compound in the organic synthesis.Cyano compound is not only important pharmaceutical intermediate; And be the important structure of colouring substance; And they are easy to be converted into other useful functional compounds; Like aldehyde, ketone, carboxylic acid, amine and acid amides etc., in organic compound molecule, introducing cyanic acid through the formation of carbon-carbon bond is one of mode the most basic in the organic synthesis.Indoles is present in the natural compounds widely, is a kind of very important heterogeneous ring compound.As containing the escitalopram of cyanic acid, lexapro is a kind of medicine of effectively depression; The not imperial femara that contains two cyanic acid is a kind of medicine that is used for the breast carcinoma of early stage assisting therapy effectively; The Kang Shide that contains cyanic acid, Casodex are used for the active drug of breast carcinoma of early stage assisting therapy.Realizing the formation of carbon on the indoles-cyanogen key through c h bond activatory method, is a kind of very effective and novel method thereby introduce cyanic acid.
The synthetic cyano compound method of reporting in the document mainly contains following several kinds:
(1) through sandmeyer reaction (Sandmeyer reaction).This reaction is the method for one type of effective synthesizing aryl nitrile compound, but because its more reactions step, reaction complicacy and productive rate are on the low side, have limited its application in synthetic.
Figure 2012102133390100002DEST_PATH_IMAGE002
(2) make up the aryl nitrile compound through aryl halide compound and cyanic acid reagent.Such reaction is simple, and single stepping just can obtain title product, and a succinct approach is provided for the aryl nitrile compound is synthetic.
Figure 2012102133390100002DEST_PATH_IMAGE004
(3) directly make up the aryl nitrile compound by guiding c h bond activatory method.This type reaction conditions is simple, and Atom economy is good, to us a good direction is provided.
Figure 2012102133390100002DEST_PATH_IMAGE006
The compound method of the preparation 3-cyanic acid substituted indole compound of reporting in the existing literature has:
(1) obtain through the reaction of 5 steps from reagent such as indoles and trifluoracetic acids, concrete reaction as follows:
Figure 2012102133390100002DEST_PATH_IMAGE008
(2) obtain 3 cyaniding products from 3-formaldehyde indoles and Potssium Cyanide and primary ammonium phosphate reaction:
Figure 2012102133390100002DEST_PATH_IMAGE010
(3) under the palladium catalysis, indoles and cuprous cyanide react and obtain:
Figure 2012102133390100002DEST_PATH_IMAGE012
(4) from 2 3-position substituted indoles, be cyano sources with DMF, obtain concrete the reaction as follows under the palladium catalysis:
Figure 2012102133390100002DEST_PATH_IMAGE014
In sum, the method for preparing the 3-cyanoindole has a lot, but these reactions have a lot of defectives; Requirement to substrate is high; Reactions step is complicated or need introduce blocking group at 2, and in reaction, is difficult to obtain the product of single 3 cyanic acidization, often is mixture.
Summary of the invention
One of the object of the invention is to provide a kind of 3-cyanic acid substituted indole compound
Two of the object of the invention is to provide a kind of preparation method of this compound.
For achieving the above object, the reaction mechanism that the inventive method adopts is:
Figure 2012102133390100002DEST_PATH_IMAGE016
R is: methoxyl group
R 1For: Ph, Bn, Allyl or n-Butyl.
According to above-mentioned reaction mechanism, the present invention has adopted following technical scheme:
A kind of 3-cyanic acid substituted indole compound is characterized in that the structural formula of this compound is:
Figure 2012102133390100002DEST_PATH_IMAGE018
Wherein: R 1For: methoxyl group; R 2For: Ph, Bn, Allyl or n-Butyl.
A kind of method for preparing above-mentioned 3-cyanic acid substituted indole compound; It is characterized in that this method has following steps: with indoles, mantoquita and tert-butyl isonitrile by 1: (2.0～3.0): the mol ratio of (2.0～3.0) is dissolved in N; In the dinethylformamide; And the palladium of adding catalyst levels, 100 oC～130 oStirring reaction to reaction raw materials disappears under the C; Remove solvent, add 3 N ammonia solns, use the ethyl acetate extraction product, organic phase is removed solvent and is got crude product after drying; This crude product promptly obtains corresponding 3 cyanic acid substituted indole compounds through separation and purification; The structural formula of described indoles is:
Figure 2012102133390100002DEST_PATH_IMAGE020
Wherein: R 1For: methoxyl group; R 2For: Ph, Bn, Allyl or n-Butyl; Described mantoquita is: trifluoracetic acid copper.
3-cyanic acid substituted indole compound of the present invention is one type of important organic reaction midbody, through dissimilar organic chemical reactionses, and like hydrolysis reaction, reduction reaction, oxidizing reaction can synthesize a series of indole derivatives quickly and easily.Relevant reaction is exemplified below:
1. under alkaline action condition, can synthesize 3-carboxamide indoles (Beevers, R. E.; Buckley, G. M. Bioorg. Med. Chem. Lett. 2006, 16,2535); In phosphoric acid buffer, utilize quinoline-degrading bacterium can obtain into acid product (Wang, M. X. Tetrahedron Lett. 1995, 36,9561):
Figure 2012102133390100002DEST_PATH_IMAGE022
Figure 2012102133390100002DEST_PATH_IMAGE024
2. utilizing 3-cyanoindole compound can pass through one type of important pharmaceutical intermediate ICS 205-930 of polystep reaction, is one type of important thrombotonin:
Figure 2012102133390100002DEST_PATH_IMAGE026
See also following document:
(1)?Swain,?C.?J.;?Baker,?R.;?Kneen,?C.;?Herbert,?R.;?Moseley,?J.;?Saunders,?J.;?Seward,?E.?M.;?Stevenson,?G.?I.;?Beer,?M.;?Stanton,?J.;?Watling,?K.;?Balls,?R.?G.? J.?Med.?Chem.? 1992,?35,?1019.
(2)?Richardson,?B.?P.;?Engel,?G.;?Donatach,?P.;?Stadler,?P.?A.? Nature,? 1985,?316,?126.
3. can synthesize ocean bisindole alkaloid Nortopsentin (Subba Reddy, B. V. through the 3-cyanoindole with remarkable anti-tumor activity; Begum, Z.; Reddy, Y. J.; Yadav, J. S. Tetrahedron Lett. 2010, 51, 3334), this Alkaloid is present in (Xiong, W. in the natural product; Yang, C.; Jiang, B. Bioorg. Med. Chem. 2001, 9, 1773):
Figure 2012102133390100002DEST_PATH_IMAGE028
The inventive method raw material is easy to get, and the novel tert-butyl isonitrile of employing is the cyanic acid source first, has avoided the use of the big metal cyanides of toxicity.Use conventional reaction solvent in the reaction, operate very simply, condition is moderate, reacts environmental protection, and productive rate reaches as high as 74%, in industrial production, has good application prospects.
Embodiment
Embodiment one: 1-phenyl-1 HThe preparation of-indoles-3-cyanic acid
1-phenyl-1 H-indoles-3-cyanic acid adopts following step: 1. in 250 milliliters of round-bottomed flasks, add 9.7 gram 1-phenyl-1 H-indoles, 560 milligrams of palladium, 43 gram additives, 12.5 gram tert-butyl isonitriles, 150 milliliters of N, dinethylformamide is heated to 130 ℃.Follow the tracks of reaction with the thin-layer chromatography method, to reaction raw materials 1-phenyl-1 H-indoles disappears; 2. after reacting end, in system, add the ammonia soln of 3 N, use the ethyl acetate extraction product, solvent is removed with Rotary Evaporators in dry back, gets crude product; 3. (sherwood oil: purifying ETHYLE ACETATE=6: 1) obtains 8.1 gram 1-phenyl-1 to crude product with column chromatography H-indoles-3-cyanic acid, productive rate are 74%.Fusing point: 120-121 ℃.
IR?(KBr,?cm -1 ):?2223,?1599,?1539,?1501,?1458,?1224,?736,?694.
1 H?NMR?(CDCl 3 ,?500?MHz):? δ?=?7.85-7.82?(m,?1H),?7.81?(s,?1H),?7.59-7.56?(m,?2H),?7.53-7.47?(m,?4H),?7.37-7.33?(m,?2H).
13 C?NMR?(CDCl 3 ,?125?MHz): δ?=?137.9,?135.7,?134.8,?130.1,?128.5,?128.1,?125.0,?124.7,?122.9,?120.1,?115.7,?111.6,?88.2.
LC/MS?m/z?(relative?intensity):?219?[M+1 +].
Embodiment two: 1-(4-fluoro-phenyl)-1 HThe preparation of-indoles-3-cyanic acid
1-(4-fluoro-phenyl)-1 H-indoles-3-cyanic acid adopts following step: 1. in 250 milliliters of round-bottomed flasks, add 10.5 gram 1-(4-fluoro-phenyl)-1 H-indoles, 560 milligrams of palladium, 43 gram additives, 12.5 gram tert-butyl isonitriles, 150 milliliters of N, dinethylformamide is heated to 130 ℃.Follow the tracks of reaction with the thin-layer chromatography method, to reaction raw materials 1-(4-fluoro-phenyl)-1 H-indoles disappears; 2. after reacting end, in system, add the ammonia soln of 3 N, use the ethyl acetate extraction product, solvent is removed with Rotary Evaporators in dry back, gets crude product; 3. (sherwood oil: purifying ETHYLE ACETATE=6: 1) obtains 7.4 gram 1-(4-fluoro-phenyl)-1 to crude product with column chromatography H-indoles-3-cyanic acid, productive rate are 63%.Fusing point: 164-167 ℃.
IR?(KBr,?cm -1 ):?2227,?1539,?1515,?1460,?1215,?837,?740.
1 H?NMR?(CDCl 3 ,?500?MHz):? δ=?7.84-7.82?(m,?1H),?7.76?(s,?1H),?7.48-7.42?(m,?3H),?7.37-7.34?(dd,? 1 J?=?6.0?Hz,? 2 J?=?3.0?Hz,?2H),?7.29-7.26?(t,? J?=?8.0?Hz,?2H).
19 F-NMR?(470?MHz,?CDCl 3 ): δ=?-112.0?(m).
13 C?NMR?(CDCl 3 ,?125?MHz): δ=?162.2?(d,? 1 J C-F ?=?248.75?Hz),?135.9,?134.8,?133.9?(d,? 4 J C-F ?=?2.5?Hz),?127.9,?127.0?(d,? 3 J C-F ?=?2.5?Hz),?124.8,?123.0,?120.2,?117.1?(d,? 2 J C-F ?=?23.75?Hz),?115.5,?111.4,?88.4.
LC/MS?m/z?(relative?intensity):?237?[M+1 +].
Anal.?Calcd.?For?C 15 H 9 FN 2 :?C,?76.26;?H,?3.84;?N,?11.86.?Found:?C,?76.39;?H,?4.001;?N,?11.98.
Embodiment three: 1-(4-methoxyl group-phenyl)-1 HThe preparation of-indoles-3-cyanic acid
1-(4-methoxyl group-phenyl)-1 H-indoles-3-cyanic acid adopts following step: 1. in 250 milliliters of round-bottomed flasks, add 11.1 gram 1-(4-methoxyl group-phenyl)-1 H-indoles, 560 milligrams of palladium, 43 gram additives, 12.5 gram tert-butyl isonitriles, 150 milliliters of N, dinethylformamide is heated to 130 ℃.Follow the tracks of reaction with the thin-layer chromatography method, to reaction raw materials 1-(4-methoxyl group-phenyl)-1 H-indoles disappears; 2. after reacting end, in system, add the ammonia soln of 3 N, use the ethyl acetate extraction product, solvent is removed with Rotary Evaporators in dry back, gets crude product; 3. (sherwood oil: purifying ETHYLE ACETATE=6: 1) obtains 4.6 gram 1-(4-methoxyl group-phenyl)-1 to crude product with column chromatography H-indoles-3-cyanic acid, productive rate are 36%.Fusing point: 126-129 ℃.
IR?(KBr,cm –1 ):?2219,?1535,?1513,?1458,?1245,?1219,?1028,?836,?754.
1 H-NMR?(500?MHz,?CDCl 3 ):? δ=?7.83-7.80?(m,?1H),?7.74?(s,?1H),?7.44-7.41?(m,?1H),?7.39-7.36?(AA’?of?AA’BB’,? J?=?9.0?Hz,?2H),?7.34-7.32?(m,?2H),?7.08-7.06?(BB’?of?AA’BB’,? J?=?8.5?Hz,?2H),?3.90?(s,?3H).
13 C-NMR?(CDCl 3 ,?125?MHz): δ=?159.6,?136.2,?135.1,?130.7,?127.9,?126.5,?124.5,?122.7,?120.0,?115.8,?115.2,?111.6,?87.5,?55.8.
LC/MS?m/z?(relative?intensity):?249?[M+1 +].
Embodiment four: the preparation of 4-methoxyl group-(1-phenyl)-1H-indoles-3-cyanic acid
4-methoxyl group-(1-phenyl)-1 H-indoles-3-cyanic acid adopts following step: 1. in 250 milliliters of round-bottomed flasks, add 11.1 gram 4-methoxyl group-(1-phenyl)-1 H-indoles, 560 milligrams of palladium, 43 gram additives, 12.5 gram tert-butyl isonitriles, 150 milliliters of N, dinethylformamide is heated to 130 ℃.Follow the tracks of reaction with the thin-layer chromatography method, to reaction raw materials 4-methoxyl group-(1-phenyl)-1 H-indoles disappears; 2. after reacting end, in system, add the ammonia soln of 3 N, use the ethyl acetate extraction product, solvent is removed with Rotary Evaporators in dry back, gets crude product; 3. (sherwood oil: purifying ETHYLE ACETATE=6: 1) obtains 6.2 gram 4-methoxyl group-(1-phenyl)-1 to crude product with column chromatography H-indoles-3-cyanic acid, productive rate are 36%.Fusing point: 105-106 ℃.
IR?(KBr,?cm –1 ):?2225,?1624,?1598,?1534,?1504,?1487,?1246,?1238,?1207,?1056,?823,?755,?700.
1 H-NMR?(500?MHz,?CDCl 3 ):? δ=?7.75?(s,?1H),?7.58-7.55?(t,? J?=?8.0?Hz,?2H),?7.49-7.46?(m,?3H),?7.41-7.39?(d,? J?=?9.0?Hz,?1H),?7.22?(d, ?J?=?2.5?Hz,?1H),?6.98-6.95?(dd,? 1 J?=?9.0?Hz,? 2 J?=?2.5?Hz,?1H),?3.91?(s,?3H).
13 C-NMR?(CDCl 3 ,?125?MHz): δ=?156.4,?138.0,?134.4,?130.5,?130.0,?128.9,?128.3,?124.7,?115.8,?115.3,?112.6,?100.9,?87.7,?55.9.
MS?(EI)?m/z?(relative?intensity):?248?(100)?[M+].
HR-MS?(ESI)?m/z?calcd?for?C 16H 12N 2O?[M +]
Embodiment five: the preparation of 1-benzyl-1H-indoles-3-cyanic acid
1-benzyl-1 H-indoles-3-cyanic acid adopts following step: 1. in 250 milliliters of round-bottomed flasks, add 10.3 gram 1-benzyls-1 H-indoles, 560 milligrams of palladium, 43 gram additives, 12.5 gram tert-butyl isonitriles, 150 milliliters of N, dinethylformamide is heated to 130 ℃.Follow the tracks of reaction with the thin-layer chromatography method, to reaction raw materials 1-benzyl-1 H-indoles disappears; 2. after reacting end, in system, add the ammonia soln of 3 N, use the ethyl acetate extraction product, solvent is removed with Rotary Evaporators in dry back, gets crude product; 3. (sherwood oil: purifying ETHYLE ACETATE=6: 1) obtains 7.1 gram 1-benzyls-1 to crude product with column chromatography H-indoles-3-cyanic acid, productive rate are 61%.Fusing point: 69-72 ℃.
IR?(KBr,?cm -1 ):?2212,?1531,?1468,?1393,?1179,?745,?735,?696.
1 H?NMR?(CDCl 3 ,?500?MHz): δ=?7.79-7.77?(m,?1H),?7.60?(s,?1H),?7.37-7.30?(m,?6H),?7.16-7.14?(d,? J?=?7.5?Hz,?2H),?5.34?(s,?2H).
13 C?NMR?(CDCl 3 ,?125?MHz): δ=?135.7,?135.3,?135.1,?129.2,?128.5,?128.1,?127.2,?124.1,?122.4,?120.1,?115.9,?111.0,?86.3,?51.0.
LC/MS?m/z?(relative?intensity):?233?[M+1 +].
Embodiment six: the preparation of 1-butyl-1H-indoles-3-cyanic acid
1-butyl-1 H-indoles-3-cyanic acid adopts following step: 1. in 250 milliliters of round-bottomed flasks, add 8.6 gram 1-butyl-1 H-indoles, 560 milligrams of palladium, 43 gram additives, 12.5 gram tert-butyl isonitriles, 150 milliliters of N, dinethylformamide is heated to 130 ℃.Follow the tracks of reaction with the thin-layer chromatography method, to reaction raw materials 1-butyl-1 H-indoles disappears; 2. after reacting end, in system, add the ammonia soln of 3 N, use the ethyl acetate extraction product, solvent is removed with Rotary Evaporators in dry back, gets crude product; 3. (sherwood oil: purifying ETHYLE ACETATE=6: 1) obtains 4.3 gram 1-butyl-1 to crude product with column chromatography H-indoles-3-cyanic acid is brown liquid, and productive rate is 43%.
IR?(KBr,?cm –1 ):?2217,?1531,?1467,?1395,?1363,?1187,?744.
1 H-NMR?(500?MHz,?CDCl 3 ):? δ?=?7.77-7.75?(d,? J?=?7.5?Hz,?1H),?7.59?(s,?1H),?7.42-7.40?(d, ?J?=?8.5?Hz,?1H),?7.35-7.32?(t,? J?=?7.5?Hz,?1H),?7.30-7.27?(t,? J?=?8.0?Hz,?1H),?4.18-4.14?(t,? J?=?7.5?Hz,?2H),?1.88-1.81?(m,?2H),?1.39-1.31?(m?,2H),?0.97-0.94?(t,? J?=?7.5?Hz,?3H).
13 C-NMR?(CDCl 3 ,?125?MHz): δ=?135.4,?134.8,?128.1,?123.8,?122.1,?120.1,?116.2,?110.7,?85.6,?47.1,?32.0,?20.1,?13.7.
MS?(EI)?m/z?(relative?intensity):?198?(45)?[M +],?155?(100).
HR-MS?(ESI)?m/z?calcd?for?C 13H 14N 2?[M +]?198.1157,?found?198.1154.
Embodiment seven: the preparation of 1-allyl group-1H-indoles-3-cyanic acid
1-allyl group-1 H-indoles-3-cyanic acid adopts following step: 1. in 250 milliliters of round-bottomed flasks, add 7.8 gram 1-allyl groups-1 H-indoles, 560 milligrams of palladium, 43 gram additives, 12.5 gram tert-butyl isonitriles, 150 milliliters of N, dinethylformamide is heated to 130 ℃.Follow the tracks of reaction with the thin-layer chromatography method, to reaction raw materials 1-allyl group-1 H-indoles disappears; 2. after reacting end, in system, add the ammonia soln of 3 N, use the ethyl acetate extraction product, solvent is removed with Rotary Evaporators in dry back, gets crude product; 3. (sherwood oil: purifying ETHYLE ACETATE=6: 1) obtains 3.8 gram 1-allyl groups-1 to crude product with column chromatography H-indoles-3-cyanic acid is brown liquid, and productive rate is 42%.
IR?(KBr,?cm –1 ):?2218,?1645,?1615,?1531,?1466,?1391,?1182,?933,?742.
1 H-NMR?(500?MHz,?CDCl 3 ): δ=?7.77?(d,? J?=?8.0?Hz,?1H),?7.61?(s,?1H),?7.39?(d,? J?=?8.0?Hz,?1H),?7.35-7.28?(m,?2H),?6.03-5.94?(m,?1H),?5.32-5.30?(d,? J?=?10.5?Hz,?1H),?5.17-5.13?(d, ?J?=?17.5?Hz,?1H),?4.77?(d,? J?=?5.5?Hz,?2H).
13 C-NMR?(CDCl 3 ,?125?MHz): δ=?135.5,?134.8,?131.8,?128.0,?124.0,?122.3,?120.1,?119.1,?116.0,?110.9,?86.1,?49.6.
LC/MS?m/z?(relative?intensity):?183?[M+1 +]。

Claims (2)

1. 3-cyanic acid substituted indole compound is characterized in that the structural formula of this compound is:
Figure 2012102133390100001DEST_PATH_IMAGE002
Wherein: R 1For: methoxyl group; R 2For: Ph, Bn, Allyl or n-Butyl.
2. method for preparing 3-cyanic acid substituted indole compound according to claim 1; It is characterized in that this method has following steps: with indoles, mantoquita and tert-butyl isonitrile by 1: (2.0～3.0): the mol ratio of (2.0～3.0) is dissolved in N; In the dinethylformamide; And the palladium of adding catalyst levels, 100 oC～130 oStirring reaction to reaction raw materials disappears under the C; Remove solvent, add 3 N ammonia solns, use the ethyl acetate extraction product, organic phase is removed solvent and is got crude product after drying; This crude product promptly obtains corresponding 3 cyanic acid substituted indole compounds through separation and purification; The structural formula of described indoles is:
Wherein: R 1For: methoxyl group; R 2For: Ph, Bn, Allyl or n-Butyl; Described mantoquita is: trifluoracetic acid copper.
CN201210213339.0A 2012-06-27 2012-06-27 3-cyan substituted indole compound and synthetic method thereof Expired - Fee Related CN102718694B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201210213339.0A CN102718694B (en) 2012-06-27 2012-06-27 3-cyan substituted indole compound and synthetic method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201210213339.0A CN102718694B (en) 2012-06-27 2012-06-27 3-cyan substituted indole compound and synthetic method thereof

Publications (2)

Publication Number Publication Date
CN102718694A true CN102718694A (en) 2012-10-10
CN102718694B CN102718694B (en) 2014-04-02

Family

ID=46944599

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201210213339.0A Expired - Fee Related CN102718694B (en) 2012-06-27 2012-06-27 3-cyan substituted indole compound and synthetic method thereof

Country Status (1)

Country Link
CN (1) CN102718694B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103467386A (en) * 2013-09-10 2013-12-25 上海大学 Aryl pyrimidine ortho-position monocyano compounds and synthesis method thereof
CN110240554A (en) * 2019-06-27 2019-09-17 上海大学 α-thioether aryl acetonitrile compound and its synthetic method

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1665809A (en) * 2001-06-21 2005-09-07 艾文蒂斯药品有限公司 Azaindoles
CN101219986A (en) * 2007-01-09 2008-07-16 上海睿智化学研究有限公司 3-cyanogen radical indole compounds and its synthetic method
CN101541748A (en) * 2006-01-13 2009-09-23 Ptc医疗公司 Methods for treating hepatitis C

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1665809A (en) * 2001-06-21 2005-09-07 艾文蒂斯药品有限公司 Azaindoles
CN101541748A (en) * 2006-01-13 2009-09-23 Ptc医疗公司 Methods for treating hepatitis C
CN101219986A (en) * 2007-01-09 2008-07-16 上海睿智化学研究有限公司 3-cyanogen radical indole compounds and its synthetic method

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103467386A (en) * 2013-09-10 2013-12-25 上海大学 Aryl pyrimidine ortho-position monocyano compounds and synthesis method thereof
CN103467386B (en) * 2013-09-10 2015-05-27 上海大学 Aryl pyrimidine ortho-position monocyano compounds and synthesis method thereof
CN110240554A (en) * 2019-06-27 2019-09-17 上海大学 α-thioether aryl acetonitrile compound and its synthetic method
CN110240554B (en) * 2019-06-27 2021-02-23 上海大学 Alpha-thioether aryl acetonitrile compound and synthetic method thereof

Also Published As

Publication number Publication date
CN102718694B (en) 2014-04-02

Similar Documents

Publication Publication Date Title
CN102030770B (en) Preparation method of aromatic boronic acid ester composite
CN105001028A (en) Synthesis method for asymmetric conjugate diyne compound
CN109575014B (en) Benzimidazo [2,1-a ] isoquinolinone compound and preparation method thereof
CN105801575A (en) Synthetic method of imidazo[1,2-a]pyridine
CN105175328A (en) Method for synthesizing quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone
CN109369610A (en) A kind of synthetic method of cyclobutanol and nitro substituted naphthol class compound
CN111362895A (en) Synthesis method of naphthofuran derivative, naphthofuran derivative and application
CN108947945B (en) 1, 3-dihydroisobenzofuran derivative and synthetic method and application thereof
CN104910104A (en) Method for synthesizing dihydrofuran derivatives under catalytic action of copper
CN107082771A (en) Double α cyano group imines substituted isochroman class compounds and its synthetic method
CN102718694B (en) 3-cyan substituted indole compound and synthetic method thereof
CN109651367B (en) Method for preparing 1, 4-dihydroquinoline and pyrrolo [1,2-a ] quinoline compounds
CN109651271B (en) Synthetic method of 3-tert-butyl-N-methylquinoxaline-2 (1H) -ketone compound
CN105272987A (en) Preparation method of 3-cyano-N-confused porphyrin compound
CN105820174A (en) Polysubstituted thienoindole derivative and preparation method thereof
CN113912609B (en) Preparation method of natural alkaloid tryptanthrin and derivatives thereof
CN105646288B (en) A kind of preparation method of carbamate derivatives
CN102702069B (en) 2-cyano-substituted indole compound and synthetic method thereof
CN107619386A (en) A kind of aromatic ring simultaneously [c] carbazole analog derivative and its synthetic method
CN103044313B (en) Method for synthesising carbazole compounds
CN108409672B (en) Method for synthesizing polysubstituted pyrimidine under catalysis of copper salt
CN109053556A (en) Pyridyl group bridging-phenyl-amino pyridine compounds and their, complex and its synthesis and application
CN113200924B (en) 4-amino-5-pyrimidine formamide compound and preparation method and application thereof
CN103664875B (en) Isosorbide-5-Nitrae, the synthetic method of 5,6-tetrahydropyrimidinederivatives derivatives
CN113024475B (en) Synthetic method of quinoxalinone compound

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20140402

Termination date: 20170627

CF01 Termination of patent right due to non-payment of annual fee