Divergent Synthesis of Novel Five-Membered Heterocyclic Compounds by Base-Mediated Rearrangement of Acrylamides Derived from a Novel Isocyanide-Based Multicomponent Reaction

doi:10.3390/molecules16108775

This article is

freely available
re-usable

Molecules 2011, 16(10), 8775-8787; doi:10.3390/molecules16108775

Article

Divergent Synthesis of Novel Five-Membered Heterocyclic Compounds by Base-Mediated Rearrangement of Acrylamides Derived from a Novel Isocyanide-Based Multicomponent Reaction

Andrea Basso* , Luca Banfi and Renata Riva

Department of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, 16146 Genova, Italy

* Author to whom correspondence should be addressed.

Received: 21 September 2011; in revised form: 3 October 2011 / Accepted: 11 October 2011 / Published: 19 October 2011

(This article belongs to the Special Issue Multicomponent Reaction)

Download PDF Full-Text [237 KB, uploaded 19 October 2011 16:50 CEST]

Abstract: We have recently reported a novel multicomponent reaction between arylacetic acids and isocyanides, affording α-acyloxyacrylamides through an unusual mechanism. The products of this novel multicomponent reaction can rearrange to five membered heterocyclic compounds when exposed to an alkaline environment. Depending on the reaction conditions and on the substitution pattern on the substrates, various pyrrolidine derivatives can be selectively obtained. We now wish to report that libraries endowed with skeletal diversity, thus responding to the requirements of Diversity Oriented Synthesis (DOS), can be efficiently prepared in this manner, and phenotypic biological assays have shown interesting properties of some representative compounds.

Keywords: multicomponent reactions; isocyanides; rearrangement reactions; diversity oriented synthesis

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

Basso, A.; Banfi, L.; Riva, R. Divergent Synthesis of Novel Five-Membered Heterocyclic Compounds by Base-Mediated Rearrangement of Acrylamides Derived from a Novel Isocyanide-Based Multicomponent Reaction. Molecules 2011, 16, 8775-8787.

AMA Style

Basso A, Banfi L, Riva R. Divergent Synthesis of Novel Five-Membered Heterocyclic Compounds by Base-Mediated Rearrangement of Acrylamides Derived from a Novel Isocyanide-Based Multicomponent Reaction. Molecules. 2011; 16(10):8775-8787.

Chicago/Turabian Style

Basso, Andrea; Banfi, Luca; Riva, Renata. 2011. "Divergent Synthesis of Novel Five-Membered Heterocyclic Compounds by Base-Mediated Rearrangement of Acrylamides Derived from a Novel Isocyanide-Based Multicomponent Reaction." Molecules 16, no. 10: 8775-8787.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert