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- Title
Synthesis of (7 S)-(−)-7-aryl-5-methyl-7-trifluoromethyl-1,3,6,7-tetrahydro-2 H-1,4-diazepin-2-ones.
- Authors
Vovk, M. V.; Golovach, N. M.; Sukach, V. A.; Chernyuk, O. N.; Manoilenko, O. V.
- Abstract
Acylation of ( S)-(−)-4-amino-4-aryl-5,5,5-trifluoropentan-2-ones with chloroacetyl chloride gave the corresponding chloroacetamides which were treated with sodium azide and then with triphenylphosphine to obtain triphenyl-λ5-phosphanylideneaminoacetic acid amides. The latter underwent thermal (boiling toluene) or base-catalyzed (NaOH/MeOH) intramolecular cyclization with elimination of triphenylphosphine oxide and formation of (7 S)-(−)-7-aryl-5-methyl-7-trifluoromethyl-1,3,6,7-tetrahydro-2 H-1,4-diazepin-2-ones.
- Subjects
ACYLATION; CHEMICAL reactions; AMIDES; TOLUENE; PHOSPHINE
- Publication
Russian Journal of Organic Chemistry, 2010, Vol 46, Issue 4, p480
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428010040044