GB1144829A - Tricyclic derivatives of acetamide - Google Patents

Abstract

1,144,829. Tricyclic derivatives of acetamide. BOEHRINGER MANNHEIM G.m.b.H. 14 Dec., 1967 [16 Dec., 1966], No. 56827/67. Heading C2C. Novel tricyclic derivatives of acetamide of the formula wherein X is a saturated or unsaturated, straightchain or branched aliphatic hydrocarbon radical containing up to 0À3 carbon atom, an oxamethylene, thiamethylene, thiaethylene radical, an optionally alkylated or acylated iminomethylene radical or an optionally alkylated carboximido group, R 1 is hydrogen or halogen atom, or a C 1-3 alkyl, alkoxy, trifluoromethyl or alkylmercapto, R 2 is hydrogen or hydroxyl, R 3 is hydrogen or C 1-3 alkyl, and R 4 is a hydrogen or, together with R 2 , represents a further valency bond, are prepared by reacting the corresponding carboxylic acids or reactive derivatives thereof with ammonia, saponifying the corresponding nitriles under mild conditions, when R 2 and R 4 represent a further valency bond by reacting a ketone of the general formula with a compound of the formula when Alk is lower alkyl and Me is an alkali metal atom, by the hydration or hydrogenation of the corresponding compounds wherein R 2 and R 4 together form a further valency bond, or the dehydration of the corresponding compounds wherein R 2 is a hydroxyl group. 5,6 - Dihydro - morphanthridin - 6 - one - 11- acetyl chloride is prepared by reacting oxalyl chloride with 5,6-dihydromorphanthridin-6-one- 11-acetic acid, resulting from the hydrolysis of the corresponding ethyl ester, which is in turn, obtained by hydrogenating 11-carbethoxymethylene - 5,6 - dihydro - morphanthridin - 6 - one obtained by reacting 5,6-dihydro-morphanthridin-6,11-dione with the sodium derivative of carbethoxymethyl-phosphonic acid diethyl ester.