Metal- and solvent-free domino reaction of 2-isocyanophenol esters to benzoxazines: long-range 1,5-acyl migration on 1,4-diazabutatriene-Reference-Cited by-同舟云学术

Metal- and solvent-free domino reaction of 2-isocyanophenol esters to benzoxazines: long-range 1,5-acyl migration on 1,4-diazabutatriene

Published:2024 Issue:41 Volume:60 Page:5451-5454
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Akbari Alireza¹,Khosravi Hormoz¹^ORCID,Bauer Felix²,Rominger Frank³,Breit Bernhard²^ORCID,Balalaie Saeed¹^ORCID

Affiliation:

1. Peptide Chemistry Research Institute, Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran

2. Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, Freiburg im Breisgau 79104, Germany

3. Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, Heidelberg D-69120, Germany

Abstract

The first example of intramolecular nucleophilic addition of 1,4-diazabutatriene to esters is disclosed. This approach provides a facile and versatile synthesis for functionalized 2H-1,4-benzoxazines through metal-, reagent-, and solvent-free conditions.

Funder

Deutsche Forschungsgemeinschaft

Iran National Science Foundation

Publisher

Royal Society of Chemistry (RSC)

Link

http://pubs.rsc.org/en/content/articlepdf/2024/CC/D4CC01214C

Reference26 articles.

1. Isocyanides in the Synthesis of Nitrogen Heterocycles

2. To each his own: isonitriles for all flavors. Functionalized isocyanides as valuable tools in organic synthesis

3. Strategies for Heterocyclic Construction via Novel Multicomponent Reactions Based on Isocyanides and Nucleophilic Carbenes

4. J.Zhu , Q.Wang and M. X.Wang , Multicomponent Reactions in Organic Synthesis , Wiley-VCH , Weinheim , 2014

5. R. P.Herrera and E.Marques-Lopez , Multicomponent Reactions: Concepts and Applications for Design and Synthesis , Wiley , Weinheim , 2015