Synthesis of 1-vinylpyrrole-2-carbonitriles

Autor:	Boris A. Trofimov, Elena V. Skital'tseva, Elena Yu. Schmidt, Andrey V. Ivanov, Al'bina I. Mikhaleva, Konstantin B. Petrushenko, Elena Yu. Senotrusova, Igor A. Ushakov, Alexander M. Vasil'tsov
Rok vydání:	2009
Předmět:	chemistry.chemical_compound Acetic anhydride Acetylene chemistry Yield (chemistry) Organic Chemistry Drug Discovery Organic chemistry Bifunctional Biochemistry
Zdroj:	Tetrahedron Letters. 50:97-100
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2008.10.104
Popis:	A new highly synthetically potent series of bifunctional pyrroles, 1-vinylpyrrole-2-carbonitriles, were synthesized from readily available 1-vinylpyrrole-2-carbaldehyde oximes by two methods: (1) reaction with acetylene (KOH/DMSO, 70 °C, 10 min, yields 58–67%) and (2) reaction with acetic anhydride (90–100 °C, 5 h, yields 83–93%). Starting from 2-phenyl-1-vinylpyrrole, the one-pot synthesis of the corresponding 1-vinyl-2-carbonitrile was accomplished directly by successive treatment with a DMF/(COCl) 2 complex, NH 2 OH·HCl/NaOAc, and acetic anhydride (yield 58%).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9a749feffc59c5b4287739b8ade41227 https://doi.org/10.1016/j.tetlet.2008.10.104 Zobrazit plný text záznamu Full Text from ScienceDirect