Literature DB >> 29808901

Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines.

Alexander V Aksenov1, Dmitrii A Aksenov, Georgii D Griaznov, Nicolai A Aksenov, Leonid G Voskressensky, Michael Rubin.   

Abstract

The polyphosphoric acid-mediated reaction of 2-(2-aminophenyl)indenes with nitroalkenes was tested in the frame of synthetic studies towards CDK inhibitors with the paullone core. Unexpectedly, this reaction proceeded via a different mechanistic pathway affording derivatives of the natural alkaloid isocryptolepine. The scope of this unusual transformation was investigated and a mechanistic rationale explaining this outcome is offered.

Entities:  

Year:  2018        PMID： 29808901     DOI： 10.1039/c8ob00588e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  4 in total

Review 1.  Isolation and synthesis of cryptosanguinolentine (isocryptolepine), a naturally-occurring bioactive indoloquinoline alkaloid.

Authors:  Elida N Thobokholt; Enrique L Larghi; Andrea B J Bracca; Teodoro S Kaufman
Journal:  RSC Adv       Date:  2020-05-19       Impact factor: 4.036

Review 2.  Advancements in the synthesis of fused tetracyclic quinoline derivatives.

Authors:  Ramadan A Mekheimer; Mariam A Al-Sheikh; Hanadi Y Medrasi; Kamal U Sadek
Journal:  RSC Adv       Date:  2020-05-27       Impact factor: 4.036

3.  Preparation of 3,5-diarylsubstituted 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones via base-assisted cyclization of 3-cyanoketones.

Authors:  Nicolai A Aksenov; Dmitrii A Aksenov; Igor A Kurenkov; Alexander V Aksenov; Anton A Skomorokhov; Lidiya A Prityko; Michael Rubin
Journal:  RSC Adv       Date:  2021-04-30       Impact factor: 4.036

4.  A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities.

Authors:  Nicolai A Aksenov; Alexander V Aksenov; Alexander Kornienko; Annelise De Carvalho; Véronique Mathieu; Dmitrii A Aksenov; Sergei N Ovcharov; Georgii D Griaznov; Michael Rubin
Journal:  RSC Adv       Date:  2018-11-01       Impact factor: 3.361
  4 in total

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