Literature DB >> 25101524

Multicomponent [5 + 2] cycloaddition reaction for the synthesis of 1,4-diazepines: isolation and reactivity of azomethine ylides.

Dong Jin Lee1, Hong Sik Han, Jinhwan Shin, Eun Jeong Yoo.   

Abstract

Air-stable azomethine ylides with an unusual pattern of charge distribution were efficiently prepared via the rhodium-catalyzed reaction between pyridines and 1-sulfonyl-1,2,3-triazoles. This reaction allowed for the first example of the catalytic multicomponent [5 + 2] cycloaddition reactions, thus resulting in the formation of biologically active 1,4-diazepine compounds.

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Year:  2014        PMID: 25101524     DOI: 10.1021/ja5061609

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  12 in total

Review 1.  Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.

Authors:  Kostiantyn O Marichev; Michael P Doyle
Journal:  Org Biomol Chem       Date:  2019-04-24       Impact factor: 3.876

Review 2.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

3.  Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs.

Authors:  Christopher J Smedley; Gencheng Li; Andrew S Barrow; Timothy L Gialelis; Marie-Claire Giel; Alessandra Ottonello; Yunfei Cheng; Seiya Kitamura; Dennis W Wolan; K Barry Sharpless; John E Moses
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-04       Impact factor: 15.336

4.  Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors:  Liangbing Fu; Huw M L Davies
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

Review 5.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

6.  A Rh(II)-catalyzed multicomponent reaction by trapping an α-amino enol intermediate in a traditional two-component reaction pathway.

Authors:  Shunying Liu; Wenfeng Yao; Yuan Liu; Qinghua Wei; Jianghui Chen; Xiang Wu; Fei Xia; Wenhao Hu
Journal:  Sci Adv       Date:  2017-03-08       Impact factor: 14.136

7.  Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of α-Imino Carbenes to Tröger Bases.

Authors:  Alessandro Bosmani; Alejandro Guarnieri-Ibáñez; Sébastien Goudedranche; Céline Besnard; Jérôme Lacour
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-14       Impact factor: 15.336

8.  Regiodivergent synthesis of pyrazino-indolines vs. triazocines via α-imino carbenes addition to imidazolidines.

Authors:  Alejandro Guarnieri-Ibáñez; Adiran de Aguirre; Céline Besnard; Amalia I Poblador-Bahamonde; Jérôme Lacour
Journal:  Chem Sci       Date:  2020-11-23       Impact factor: 9.825

9.  Tandem 1,2-sulfur migration and (aza)-Diels-Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes.

Authors:  Dongari Yadagiri; Pazhamalai Anbarasan
Journal:  Chem Sci       Date:  2015-07-10       Impact factor: 9.825

Review 10.  1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives.

Authors:  Adam G Meyer; John H Ryan
Journal:  Molecules       Date:  2016-07-23       Impact factor: 4.411

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