Literature DB >> 25625884

Three-component reaction toward polyannulated quinazolinones, benzoxazinones, and benzothiazinones.

Denis Kröger1, Torben Schlüter, Malte Fischer, Irina Geibel, Jürgen Martens.   

Abstract

An efficient conversion of readily accessible cyclic imines with acid chlorides, that are able to take part in nucleophilic aromatic substitution (SNAr) reactions is realized in a new three-component, one-pot reaction, giving at least tricyclic annulated quinazolinones, benzoxazinones, and benzothiazinones as a result of the employed nitrogen, oxygen, or sulfur nucleophiles, respectively. Especially in the case of quinazolinones, this convenient strategy enables the access to heterocycles of heightened diversity, which offer the development of efficient derivatizations of the elaborated heterocyclic scaffolds. In a subsequent Heck or Ullmann cyclization, further annulations to the mentioned quinazolinones can be carried out.

Entities:  

Keywords:  Heck; Ullmann; cyclic imines; heterocycles; multicomponent reaction; polyannulation

Mesh:

Substances:

Year:  2015        PMID: 25625884     DOI: 10.1021/co500165a

Source DB:  PubMed          Journal:  ACS Comb Sci        ISSN: 2156-8944            Impact factor:   3.784


  2 in total

Review 1.  Recent advances in the development of polycyclic skeletons via Ugi reaction cascades.

Authors:  Jie Lei; Jiang-Ping Meng; Dian-Yong Tang; Brendan Frett; Zhong-Zhu Chen; Zhi-Gang Xu
Journal:  Mol Divers       Date:  2018-01-16       Impact factor: 2.943

2.  Crystal structures of two 2,3-diaryl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-ones.

Authors:  Hemant P Yennawar; Michaela J Buchwalter; Baylee K Colburn; Lee J Silverberg
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-02-20
  2 in total

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