Studies on Isocyanides and Related Compounds. N,N'-disubstituted 2-cyanoacetoxy-2-cyanomethylmalondiamides from an unusual reaction between isocyanides and cyanoacetic acid-Reference-Cited by-同舟云学术

Studies on Isocyanides and Related Compounds. N,N'-disubstituted 2-cyanoacetoxy-2-cyanomethylmalondiamides from an unusual reaction between isocyanides and cyanoacetic acid

Published:2001-11 Issue:11 Volume:2001 Page:465-467
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Marcaccini Stefano¹,Pepino Roberto¹,Paoli Paola²,Rossi Patrizia²,Torroba Tomás³

Affiliation:

1. Dipartimento di Chimica Organica “Ugo Schiff”, Università di Firenze, via Gino Capponi 9, I-50121 Firenze, Italy

2. Dipartimento di Energetica “Sergio Stecco”, Università di Firenze, via S. Marta 3, I-50139 Firenze, Italy

3. Departamento de Química, Facultad de Ciencias, Universidad de Burgos, E-09001 Burgos, Spain

Abstract

The reaction between cyanoacetic acid 1 and isocyanides 2 afforded the unexpected N,N'-disubstituted 2-cyanoacetoxy-2-cyanomethylmalondiamides 3 which were easily cleaved in very mild conditions to the corresponding 2-hydroxy derivatives 4. The structure of compound 4a was confirmed by X-ray analysis. A hypothesis for the mechanism of formation of compounds 3 is presented.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/030823401103168695

Reference18 articles.

1. Synthese von amiden aus carbonsäuren und aminen in gegenwart von isocyaniden

2. Beitrag zur Isonitril-Chemie

3. Isonitrile, VII. Einstufige Synthese von α‐Hydroxysäure‐amiden durch Abwandlung der Passerini‐Reaktion

4. Säure-katalysierte Oxidation von Isonitrilen durch Dimethylsulfoxid

5. Studies on isocyanides and related compounds: synthesis of benzo[c]thiophenes by way of acid-induced three-component reactions

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