Literature DB >> 20000445

Microwave-assisted domino and multicomponent reactions with cyclic acylketenes: expeditious syntheses of oxazinones and oxazindiones.

Marc Presset1, Yoann Coquerel, Jean Rodriguez.   

Abstract

The microwave-assisted Wolff rearrangement of cyclic 2-diazo-1,3-diketones in the presence of aldehydes and primary amines provides a straightforward access to functionalized bi- and pentacyclic oxazinones following an unprecedented three-component domino reaction. Alternatively, in the presence of acyl azides, an efficient Curtius/Wolff/hetero-Diels-Alder sequence allows the direct synthesis of oxazindiones.

Entities:  

Year:  2009        PMID: 20000445     DOI: 10.1021/ol9024056

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  Metal-free [3 + 2 + 1]/[2 + 2 + 1] biscyclization: stereospecific construction with concomitant functionalization of indolizin-5(1H)-one.

Authors:  Tuan-Jie Li; Zhong-Qiu Liu; Hong-Mei Yin; Chang-Sheng Yao; Bo Jiang; Xiang-Shan Wang; Shu-Jiang Tu; Xiu-Ling Li; Guigen Li
Journal:  J Org Chem       Date:  2013-11-07       Impact factor: 4.354

3.  Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases.

Authors:  Svetlana O Kasatkina; Ekaterina E Stepanova; Maksim V Dmitriev; Ivan G Mokrushin; Andrey N Maslivets
Journal:  Beilstein J Org Chem       Date:  2018-07-11       Impact factor: 2.883

4.  Rh(III)-Catalyzed C-H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides.

Authors:  Youpeng Zuo; Xinwei He; Yi Ning; Yuhao Wu; Yongjia Shang
Journal:  ACS Omega       Date:  2017-11-30

Review 5.  Recent advances in the chemistry of imine-based multicomponent reactions (MCRs).

Authors:  Lokman H Choudhury; Tasneem Parvin
Journal:  Tetrahedron       Date:  2011-07-18       Impact factor: 2.457

6.  Periselectivity in the Aza-Diels-Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study.

Authors:  Marc Presset; Michel Rajzmann; Guillaume Dauvergne; Jean Rodriguez; Yoann Coquerel
Journal:  Molecules       Date:  2020-10-20       Impact factor: 4.411

  6 in total

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