Spiro(pyrrolidinyl-2,3'-benzodiazepines) related to MK-329

DÖNDAŞ H. A., Grigg R., ThorntonPett M.

TETRAHEDRON, vol.52, no.42, pp.13455-13466, 1996 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 52 Issue: 42
  • Publication Date: 1996
  • Doi Number: 10.1016/0040-4020(96)00806-x
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.13455-13466
  • Çukurova University Affiliated: No

Abstract

Imines of 1-ethyl-3-amino-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepine-2-one undergo thermal (toluene, 110 degrees C) or LiBr-DBU catalysed (MeCN, room temperature) regio- and stereo-specific cycloaddition to a range of achiral and chiral dipolarophiles giving racemic and homochiral spiro (pyrrolidinyl-2,3'-benzodiazepine) cycloadducts respectively in excellent yield. The reactions proceed via intermediate NH azomethine ylides and lithe azomethine ylides respectively. Copyright (C) 1996 Elsevier Science Ltd