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Müller, T. J. J.: 2014 Science of Synthesis, 2013/6: Multicomponent Reactions, Volume 2 DOI: 10.1055/sos-SD-211-00020
Multicomponent Reactions, Volume 2

2.1.3 With Isocyanide Participation

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Book

Editor: Müller, T. J. J.

Authors: Alavijeh, N. S.; Arndtsen, B. A.; Balalaie, S.; Bonne, D.; Chen, C.; Coquerel, Y.; Elliott, M.; Festa, A.; Fusano, A.; Ghabraie, E.; Jones, D. H.; Modha, S.; Müller, T. J. J.; Purushothaman, S.; Raghunathan, R.; Rodriguez, J.-A.; Ryu, I.; Sarvary, A.; Shaabani, A.; Shaabani, S.; Szabó, K. J.; Takasu, K.; Tjutrins, J.; Van der Eycken, E.; Voskressensky, L.; Wan, J.; Xi, C.

Title: Multicomponent Reactions, Volume 2

Subtitle: Reactions Involving an α,α-Unsaturated Carbonyl Compound as Electrophilic Component, Cycloadditions, and Boron-, Silicon-, Free-Radical-, and Metal-Mediated Reactions

Print ISBN: 9783131728319; Online ISBN: 9783132064317; Book DOI: 10.1055/b-003-125831

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Multicomponent Reactions

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

Isocyanide-based multicomponent reactions represent a very important synthetic method for the synthesis of heterocyclic compounds with potential biological and medicinal activities. The nucleophilic property of isocyanides makes them a popular reactant class for the development of novel multicomponent reactions. One of the isocyanide-based multicomponent reaction approaches involves the generation of a dipolar intermediate by the addition of isocyanides to electron-deficient α, β-unsaturated carbonyl compounds such as dialkyl acetylenedicarboxylates; the dipolar intermediate can then be captured efficiently by various dipolarophiles such as CH-, NH-, and OH-acids, electron-deficient alkenes, and imines to form diverse cycloadducts.

Key words

isocyanides - α, β-unsaturated carbonyl compounds - dialkyl acetylenedicarboxylates - dipolar intermediates - dipolarophiles - heterocycles
 
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