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Synthesis of 1,2-Dihydrobenz[c]azepin-3-one via Acid-catalyzed Cyclization of N-Arylmethyl-N-methyl-3-phenylsulfanylacrylamide
- Source :
- HETEROCYCLES. 57:1063
- Publication Year :
- 2002
- Publisher :
- The Japan Institute of Heterocyclic Chemistry, 2002.
-
Abstract
- Treatment of N-arylmethyl-N-methyl-cis-3-phenylsulfanyl acrylamide (5) with p-toluenesulfonic acid induced two reactions; cyclization to 1,2-dihydrobenz[c]azepin-3-ones (7) and N-dearylmethylation to N-methylacrylamides (9 and 10) depending on the structures of the substrates. The route provides a simple method of preparing 6-methoxy- (7e), 8-methoxy- (7d), 6,8-dimethoxy- (7f), and 8,9-dimethoxy-N-methyl-1,2-dihydrobenz-[c]azepin-3-ones (7g), although the scope is limited by some side reactions.
Details
- ISSN :
- 03855414
- Volume :
- 57
- Database :
- OpenAIRE
- Journal :
- HETEROCYCLES
- Accession number :
- edsair.doi...........442f11539c8ab0a31d5119d9e5cc9b59