Synthesis of Highly Substituted Pyridines via [4 + 2] Cycloadditions of Vinylallenes and Sulfonyl Cyanides

Autor:	Philip J. Hamzik, Christian Gomez, Rick L. Danheiser, Leandro Espindola, Samuel G. Bartko
Rok vydání:	2019
Předmět:	Sulfonyl chemistry.chemical_classification Nucleophile chemistry 010405 organic chemistry Nucleophilic aromatic substitution Organic Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences
Zdroj:	The Journal of Organic Chemistry. 85:548-563
ISSN:	1520-6904 0022-3263
Popis:	A convergent strategy for the synthesis of multisubstituted pyridines is described. Vinylallenes combine with commercially available arylsulfonyl cyanides in Diels-Alder cycloadditions to generate isopyridine cycloadducts that are converted to pyridines upon further heating or addition of a base. The 2-sulfonylpyridine products undergo nucleophilic aromatic substitution reactions with oxygen and carbon nucleophiles to provide access to a variety of highly substituted pyridines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9e13a3363a9c39d6d9d64756ae3f5188 https://doi.org/10.1021/acs.joc.9b02628 Zobrazit plný text záznamu