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Synthesis 2012(4): 547-550  
DOI: 10.1055/s-0031-1289673
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Bogdan Draghicia, Bahaa El-Dien M. El-Gendya,b, Alan R. Katritzky*a,c
a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
b Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt
c Department of Chemistry, King Abdulaziz University, Jeddah 21589, Saudi Arabia
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;
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Publikationsverlauf

Received 20 October 2011
Publikationsdatum:
23. Januar 2012 (online)

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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.

Key words

N,O-heterocycles - rearrangements - benzoxazines - quinazolines - benzothiazines

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