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Synthesis 2005(11): 1876-1880  
DOI: 10.1055/s-2005-870006
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of 6′-Amino-Substituted Spirooxazines

A. V. Koshkina, V. Lokshinb, A. Samatb, S. P. Gromova, O. A. Fedorova*a
a Photochemistry Center of the Russian Academy of Sciences, Novatorov str. 7a, 119421 Moscow, Russia
Fax: +7(095)9361255; e-Mail: fedorova@photonics.ru ;
b Faculté des Sciences de Luminy, Université de la Méditerranée, UMR 6114 CNRS, 13288 Marseille, France
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Publication History

Received 11 November 2004
Publication Date:
29 June 2005 (online)

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Abstract

A one-pot synthesis of 6′-amino-substituted spiroindolinonaphth[2,1-b][1,4]oxazines is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-amino-2-naphthol in the presence of different secondary amines and oxidizing agents using methanol or toluene as the solvent. The main advantage of the method is its simplicity, and starting from readily accessible reagents, it allows the preparation of amino derivatives of spironaphthoxazine with good yields under mild reaction conditions.

Key words

spiroindolinonaphth[2,1-b][1,4]oxazine - 2-methylene-1,3,3-trimethylindoline - 1-amino-2-naphthol - one-pot synthesis

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