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, cilt.2018, ss.362-374, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 2018
  • Basım Tarihi: 2018
  • Doi Numarası: 10.24820/ark.5550190.p010.374
  • Dergi Adı: ARKIVOC
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.362-374
  • Anahtar Kelimeler: Nitration, N-oxidation, 6-bromoquinoline, aminoquinoline, quinoline N-oxides, morpholinyl and piperazinyl quinolines, REGIOSELECTIVE BROMINATION, ANTICANCER ACTIVITIES, DERIVATIVES, AGENTS
  • Yıldız Teknik Üniversitesi Adresli: Evet

Özet

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.