Literature DB >> 26250789

[3 + 2] Cycloaddition/Oxidative Aromatization Sequence via Photoredox Catalysis: One-Pot Synthesis of Oxazoles from 2H-Azirines and Aldehydes.

Ting-Ting Zeng1, Jun Xuan1, Wei Ding1, Kuan Wang1, Liang-Qiu Lu1, Wen-Jing Xiao1.   

Abstract

A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from easily accessible 2H-azirines and aldehydes under mild reaction conditions. The potential of this strategy was further demonstrated by the rapid synthesis of a cyclooxygenase-2 inhibitor as well as the success of employing electron-deficient alkenes and imines as the reaction partners.

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Year:  2015        PMID: 26250789     DOI: 10.1021/acs.orglett.5b01994

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


  8 in total

1.  Continuous multistep synthesis of 2-(azidomethyl)oxazoles.

Authors:  Thaís A Rossa; Nícolas S Suveges; Marcus M Sá; David Cantillo; C Oliver Kappe
Journal:  Beilstein J Org Chem       Date:  2018-02-23       Impact factor: 2.883

2.  Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles.

Authors:  Raju Jannapu Reddy; Matthew P Ball-Jones; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-19       Impact factor: 15.336

Review 3.  Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions.

Authors:  Katia Martina; Silvia Tagliapietra; Valery V Veselov; Giancarlo Cravotto
Journal:  Front Chem       Date:  2019-02-26       Impact factor: 5.221

4.  A facile photochemical strategy for the synthesis of high-performance amorphous MoS2 nanoparticles.

Authors:  Haifeng Sun; Manlin Yang; Shan Pu; Lichen Gou; Caizhi Lv; Juan He; Xiandeng Hou; Kailai Xu
Journal:  Nanoscale Adv       Date:  2021-03-26

5.  Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds.

Authors:  Pavel A Sakharov; Nikolai V Rostovskii; Alexander F Khlebnikov; Mikhail S Novikov
Journal:  Molecules       Date:  2022-09-02       Impact factor: 4.927

6.  Gold-catalyzed synthesis of oxazoles from alkynyl triazenes and dioxazoles.

Authors:  Zhenjun Mao; Hao Zeng
Journal:  RSC Adv       Date:  2022-08-31       Impact factor: 4.036

Review 7.  Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry.

Authors:  Michael K Bogdos; Emmanuel Pinard; John A Murphy
Journal:  Beilstein J Org Chem       Date:  2018-08-03       Impact factor: 2.883

8.  Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate.

Authors:  Mysore Bhyrappa Harisha; Pandi Dhanalakshmi; Rajendran Suresh; Raju Ranjith Kumar; Shanmugam Muthusubramanian
Journal:  Beilstein J Org Chem       Date:  2020-08-31       Impact factor: 2.883

  8 in total

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