Activation of 6-bromoquinoline by nitration: synthesis of morpholinyl and piperazinyl quinolines


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ÇAKMAK O. , Okten S., Alimli D., Saddiqa A., Ersanli C. C.

ARKIVOC, vol.2018, pp.362-374, 2018 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2018
  • Publication Date: 2018
  • Doi Number: 10.24820/ark.5550190.p010.374
  • Journal Name: ARKIVOC
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.362-374
  • Keywords: Nitration, N-oxidation, 6-bromoquinoline, aminoquinoline, quinoline N-oxides, morpholinyl and piperazinyl quinolines, REGIOSELECTIVE BROMINATION, ANTICANCER ACTIVITIES, DERIVATIVES, AGENTS

Abstract

Quinoline forms the key skeletal component of a number of important natural products and pharmacologically-active compounds. Despite a tremendous amount of research pertaining to the derivatization of quinoline, very few general synthetic routes are described in the literature starting from quinoline or tetrahydroquinoline. A simple and convenient method for the polyfunctionalization of quinolines via nitration of bromoquinolines has been developed. This method represents a new synthetic approach to convert brominated nitroquinoline derivatives into useful cyclic amines via nucleophilic-substitution (SNAr) reaction.