Literature DB >> 12688810

1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides.

Stefano Marcaccini1, Daniel Miguel, Tomás Torroba, María García-Valverde.   

Abstract

The intramolecular Ugi four-component condensation between 6-oxo-4-thiacarboxylic acids, benzylamines, and cyclohexyl isocyanide gave hexahydro-1,4-thiazepin-5-ones and 1,4-benzothiazepin-5-ones, in some cases with high stereoselectivity, and the intramolecular Passerini three-component reaction, in the presence of catalytic amine, gave tetracyclic 1,4-benzothioxepin orthoamides.

Entities:  

Year:  2003        PMID: 12688810     DOI: 10.1021/jo026614z

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

Review 1.  Emerging molecular diversity from the intra-molecular Ugi reaction: iterative efficiency in medicinal chemistry.

Authors:  Christopher Hulme; Justin Dietrich
Journal:  Mol Divers       Date:  2009-02-11       Impact factor: 3.364

2.  Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids.

Authors:  Răzvan C Cioc; Verónica Estévez; Daan J van der Niet; Christophe M L Vande Velde; Nikolaus G Turrini; Mélanie Hall; Kurt Faber; Eelco Ruijter; Romano V A Orru
Journal:  European J Org Chem       Date:  2017-03-08

3.  A N,N'-dioxide/Mg(OTf)2 complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates.

Authors:  Weiwei Luo; Xiao Yuan; Lili Lin; Pengfei Zhou; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2016-04-22       Impact factor: 9.825

Review 4.  The 100 facets of the Passerini reaction.

Authors:  Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal:  Chem Sci       Date:  2021-09-30       Impact factor: 9.825

5.  Three-Component Synthesis of Some New Coumarin Derivatives as Anticancer Agents.

Authors:  Latifah A Alshabanah; Laila A Al-Mutabagani; Sobhi M Gomha; Hoda A Ahmed
Journal:  Front Chem       Date:  2022-01-25       Impact factor: 5.221

  5 in total

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