A Short‐Cut to Substituted Fused Pyrrolo[2,1‐<i>c</i>][1,4]oxazines: A Hybrid Theoretical and Experimental Study-Reference-Cited by-同舟云学术

A Short‐Cut to Substituted Fused Pyrrolo[2,1‐c][1,4]oxazines: A Hybrid Theoretical and Experimental Study

Published:2023-06 Issue:8 Volume:12 Page:
ISSN:2193-5807
Container-title:Asian Journal of Organic Chemistry
language:en
Short-container-title:Asian J Org Chem

Author:

Ivanov Andrey V.¹^ORCID,Bobkov Alexander S.²^ORCID,Martynovskaya Svetlana V.¹^ORCID,Budaev Arsalan B.¹^ORCID,Vitkovskaya Nadezhda M.²^ORCID

Affiliation:

1. Laboratory of Heterocyclic Compounds Favorsky Irkutsk Institute of Chemistry Siberian Branch of the Russian Academy of Sciences 1 Favorsky St. 664033 Irkutsk Russian Federation

2. Laboratory of Quantum Chemical Modeling of Molecular Systems Irkutsk State University 1 Karl Marx St. 664003 Irkutsk Russian Federation

Abstract

AbstractThe effect of substituents in the pyrrole ring and at the triple bond on the formation of fused pyrrolooxazines from 1H‐pyrrol‐2‐ylmethanols and propargyl chlorides has been theoretically and experimentally studied. The energy characteristics of the reaction are evaluated using quantum‐chemical calculations (CBS‐Q//B3). A one‐pot transition metal‐free synthesis of substituted 3‐methyl‐1H‐pyrrolo[2,1‐c][1,4]oxazines in good yields has been implemented in the superbasic system NaOH/DMSO.

Funder

Ministry of Science and Higher Education of the Russian Federation

Publisher

Wiley

Subject

Organic Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ajoc.202300153

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