Condensation of Indoline with Some 1,2-and 1,3-Diketones


KILIÇ H., AYDIN Ö., Bayindir S., SARAÇOĞLU N.

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.53, no.6, pp.2096-2101, 2016 (SCI-Expanded, Scopus)

  • Publication Type: Article / Article
  • Volume: 53 Issue: 6
  • Publication Date: 2016
  • Doi Number: 10.1002/jhet.2580
  • Journal Name: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.2096-2101
  • Ankara University Affiliated: No

Abstract

Bismuth nitrate catalyzed condensation reactions of indoline with 1,2- and 1,3-diketones were investigated and were reported to proceed via different reaction pathways with the involvement of one or two of the carbonyl groups. While the reaction of indoline with cyclohexane-1,3-dione (4) gave solely condensation product, the reaction between the acetylacetone (5) and indoline provided N-acetyl indoline as single products on retro-aldol process. In contrast to 1,3-diketones, the reaction with benzil (17) was performed under difficult conditions and proceeded to give secondary products.