Synthesis of Benzoxazines, Quinazolines and 4H-Benzo[e][1,3]thiazine by ANRORC Rearrangements of 1,2,4-Oxadiazoles

Abstract 1,2,4-Oxadiazoles undergo ANRORC (Addition of Nucleophile, Ring-Opening and Ring-Closure) rearrangements upon reaction with excess of N-butyllithium to give benzoxazines, benzothiazines, and quinazolines in good yields under mild conditions.

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2012-02, Vol.44 (4), p.547-550
Main Authors: Draghici, Bogdan, El-Gendy, Bahaa El-Dien, Katritzky, Alan R.
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Description
Summary:Abstract 1,2,4-Oxadiazoles undergo ANRORC (Addition of Nucleophile, Ring-Opening and Ring-Closure) rearrangements upon reaction with excess of N-butyllithium to give benzoxazines, benzothiazines, and quinazolines in good yields under mild conditions.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1289673