1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: Chemoselective Non-Metal-Catalyzed Carboxamidation of Indoles-Reference-Cited by-同舟云学术

1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: Chemoselective Non-Metal-Catalyzed Carboxamidation of Indoles

Published:2022-02-03 Issue:07 Volume:33 Page:689-693
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Soni Jigar Y.¹,Vala Anand²¹^ORCID,Parmar Deepa²¹,Rayani Rahul²¹,Kusurkar Rakesh²¹,Guduru Ramakrishna^ORCID,Kaneriya Uttam²,Gondaliya Uday²,Parmar Nirali²

Affiliation:

1. Department of Chemistry, Faculty of Science, The Madhav University

2. Piramal Discovery Solutions, Pharmaceutical Special Economic Zone

Abstract

Abstract1,4,2-Dioxazol-5-ones are known to undergo decarboxylation under thermal conditions followed by Lossen’s rearrangement to give isocyanates. Described herein is the in situ trapping of the isocyanates by indoles to give indole-3-carboxamides in good to excellent yields.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0041-1737338.pdf

Reference5 articles.

1. Isocyanatophosphoryl Dichloride as Reagent for Introduction of Carbamoyl Group into Molecules of π-Excessive Heterocycles and Enamines

2. Acylative Coupling of Amine and Indole Using Chloroform as a Carbonyl Group

3. Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

4. 1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides

5. Rhodium(III)-Catalyzed Controllable C−H Bond Functionalization of Benzamides and Vinylidenecyclopropanes: A Directing Group Determined Reaction Pathway

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