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Issue 6, 2018
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Ultrasound-assisted one-pot multicomponent 1,3-dipolar cycloaddition strategy: combinatorial synthesis of spiro-acenaphthylene-S,S-acetal and 2H-pyranone derivatives

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Abstract

The stereo/regio/chemoselective syntheses of a library of novel spiro[acenaphthylene-1,3′-pyrrolizin]-2-one and spiro[acenaphthylene-1,5′-pyrrolo[1,2-c]thiazol]-2-one have been achieved through 1,3-dipolar cycloaddition. Intermediate azomethine ylides generated in situ from α-amino acids and acenaphthylene-1,2-dione react with α-aroylidine ketenedithioacetal (AKDTA) derivatives to give the target product in excellent yield under ultrasound irradiation. Further, spiro-S,S-acetals are converted to spiro-2H-pyranones by a one-pot cyclization strategy.

Graphical abstract: Ultrasound-assisted one-pot multicomponent 1,3-dipolar cycloaddition strategy: combinatorial synthesis of spiro-acenaphthylene-S,S-acetal and 2H-pyranone derivatives

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Supplementary files

Article information


Submitted
27 Nov 2017
Accepted
01 Feb 2018
First published
02 Feb 2018

New J. Chem., 2018,42, 4061-4066
Article type
Paper

Ultrasound-assisted one-pot multicomponent 1,3-dipolar cycloaddition strategy: combinatorial synthesis of spiro-acenaphthylene-S,S-acetal and 2H-pyranone derivatives

S. Thimmarayaperumal and S. Shanmugam, New J. Chem., 2018, 42, 4061
DOI: 10.1039/C7NJ04627H

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