Literature DB >> 26467532

Rhodium(II)-Catalyzed Formal [3 + 2] Cycloaddition of N-Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3-Aminopyrroles.

Xiaoqiang Lei1,2, Longbo Li2, Yu-Peng He1, Yefeng Tang2,3.   

Abstract

A novel rhodium(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles has been achieved that provides an efficient method for the synthesis of polysubstituted 3-aminopyrrole derivatives. An operationally simple one-pot synthesis of the titled compounds from terminal alkynes, tosyl azide, and isoxazoles was also developed. The presented reaction affords an illustrative example of employing 1,2,3-triazoles as the [2C]-component in relevant cycloaddition reactions.

Entities:  

Year:  2015        PMID: 26467532     DOI: 10.1021/acs.orglett.5b02570

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


  6 in total

1.  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

2.  Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone.

Authors:  Fenghai Guo; Matthew A McGilvary; Malcolm C Jeffries; Briana N Graves; Shekinah A Graham; Yuelin Wu
Journal:  Molecules       Date:  2017-05-01       Impact factor: 4.411

3.  Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes.

Authors:  Olga Bakhanovich; Viktor Khutorianskyi; Vladimir Motornov; Petr Beier
Journal:  Beilstein J Org Chem       Date:  2021-02-18       Impact factor: 2.883

4.  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

5.  Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids.

Authors:  Yuanhao Wang; Yunfei Wu; Yuanhe Li; Yefeng Tang
Journal:  Chem Sci       Date:  2017-03-15       Impact factor: 9.825

6.  Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes.

Authors:  Alejandro Guarnieri-Ibáñez; Florian Medina; Céline Besnard; Sarah L Kidd; David R Spring; Jérôme Lacour
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

  6 in total

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