Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds


Demir A., Akhmedov I., Sesenoglu O.

TETRAHEDRON, vol.58, no.49, pp.9793-9799, 2002 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 49
  • Publication Date: 2002
  • Doi Number: 10.1016/s0040-4020(02)01298-x
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.9793-9799
  • Keywords: nitrogen heterocycles, pyrroles, enamine esters, cyclization, POTENTIAL ANTIVIRAL AGENTS, BETA-AMINO ALCOHOLS, ACYCLIC DERIVATIVES, HOMOCHIRAL AMINES, ALPHA, KETONES, ACIDS, GLYCOSIDOPYRROLES, CONVERSION, ANALOGS
  • Middle East Technical University Affiliated: Yes

Abstract

2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into beta-enamino, beta-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared in good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.