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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 2
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Original Articles

Microwave-Assisted Solvent-Free Synthesis of the Substituted Spiroindolinonaphth[2,1-b][1,4]oxazines

A. V. Koshkin Center of Photochemistry of the Russian Academy of Sciences, Novatorov Str. 7a, 119421, Moscow, Russia
,
O. A. Fedorova Center of Photochemistry of the Russian Academy of Sciences, Novatorov Str. 7a, 119421, Moscow, RussiaCorrespondence[email protected]
,
V. Lokshin Faculté des Sciences de Luminy, Université de la Méditerraneé, Marseille, France
,
R. Guglielmetti Faculté des Sciences de Luminy, Université de la Méditerraneé, Marseille, France
,
J. Hamelin Synthèse et Electrosynthèse Organique 3, Université de Rennes 1, Campus de Beaulieu, Rennes, France
,
F. Texier-Boullet Synthèse et Electrosynthèse Organique 3, Université de Rennes 1, Campus de Beaulieu, Rennes, France
&
S. P. Gromov Center of Photochemistry of the Russian Academy of Sciences, Novatorov Str. 7a, 119421, Moscow, Russia
 show all
Pages 315-322 | Received 30 Apr 2003, Published online: 18 Oct 2011
 
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Abstract

The synthesis of the substituted spiroindolinonaphth[2,1-b][1,4]oxazines 3a–e is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-nitroso-2-naphthol under microwave irradiation. In the same conditions, in presence of morpholine the 6′-morpholinosubstituted compounds 4a, b, d, e are formed. The main advantages of the method are the short reaction time, solvent-free reaction condition, cleaner reaction products and the higher product yields in comparison with known methods of synthesis.

Acknowledgment

The study was supported by the INTAS (Grant 97-31193 and YSF 2001/2-180), PICS 705, RFBR (Grant 02-03-33058) and Russian Academy of Sciences.

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