Synthesis of New Fused 1,5-Benzodiazepines, Part 3

• Published in: Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2005-08, Vol.180 (8), p.1893-1907
• Main Author: Khodairy, A.
• Format: Article
• Language: English
• Subjects: 1,3-Dihydro-4-phenyl-1,5-benzodiazepin-2-one; oxazinobenzodiazepines; pyridobenzodiazepines; pyrimidobenzodiazepines; thiazinobenzodiazepines; thienobenzodiazepines
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/104265090889611

1,3-Dihydro-4-phenyl-1,5-benzodiazepin-2-one 1 a was treated with some ylidenecyanothioacetamides to give the corresponding pyrido(2,3-b)benzodiazepines 3- 6. Treatment of compound 1 a with a mixture of thiophen-2-aldehyde and thiourea or guanidine gave the corresponding 1,3-thiazino- and pyrimido(4,5-b)benzodiazepines 7 and 8. 3-Arylidene derivatives 9 a-e and 10 were synthesized. Compound 10 was subject to react with 2-(1-methylthio-1′-anilinomethylidene)malononitrile to give oxazino-benzodiazepine 11. Thieno(3,2-b)benzodiazepines 12 a,b and 13 were synthesized via the reaction of compound 1 b with sulfur and some active nitriles. [1,3-Dihydro-4-phenyl(1,5)-benzodiazepin-2-ylidene]malononitrile 15was used as synthon to obtain novel pyrido-, pyrano-, benzo-, and thienobenzodiazepines 16-20, respectively. The reaction of compound 1 b with CS 2 or PhNCS along with 1,1,3-tricyano-2-aminoprop-1-ene, 2-(1-methylthio-1′-anilinomethylidene)malononitrile, or 1,3-dibromopropane gave the corresponding polyfused benzodiazepines 21- 23, respectively. *For Part 1 and Part 2, see references 7 and 8.