Benzotriazole-mediated amidoalkylations of nitroalkanes, nitriles, alkynes and esters

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Katritzky A. R., Abdel-Fattah A. A. A., Celik I.

ARKIVOC, vol.2007, pp.96-113, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2007
  • Publication Date: 2007
  • Doi Number: 10.3998/ark.5550190.0008.b09
  • Journal Name: ARKIVOC
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.96-113
  • Keywords: amidoalkylation, N-(beta-nitroalkyl) amides, N-(beta-cyanoalkyl)-amides, N-acylpropargylamines, beta-N-acylamino acids, AMINO-ACID-DERIVATIVES, HIGHLY EFFICIENT SYNTHESIS, ALPHA-AMIDOALKYLATION, ENANTIOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, PARHAM CYCLIZATION, CHEMISTRY, REAGENTS, PROPARGYLAMINES, ALDEHYDE
  • Anadolu University Affiliated: Yes

Abstract

Reactions of readily available and stable N-(alpha-amidoalkyl)benzotriazoles 1 ( derived from a variety of aliphatic, aromatic or heterocyclic aldehydes) with diverse nitroalkanes, nitriles, alkynes and esters afforded N-(beta-nitroalkyl) amides 4 (54-96%), N-(beta-cyanoalkyl) amides 6 (58-88%), N- acylpropargylamines 11 (41-87%) and esters of beta-N-acylamino acids 13 (68-96%), respectively.