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

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.

Keywords:

• Microwave irradiation
• Spirooxazines
• Solvent-free 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.