Reaction of tosylmethyl isocyanide with methyl 3-substituted propiolates as acetylenic Michael acceptors

Autor:	Hideaki Sasaki, Tokujiro Kitagawa, H. Saikachi
Rok vydání:	1979
Předmět:	Dimethyl acetylenedicarboxylate chemistry.chemical_classification Acrylate Base (chemistry) Methyl propiolate General Chemistry General Medicine Medicinal chemistry Cycloaddition Adduct chemistry.chemical_compound chemistry Drug Discovery Michael reaction Organic chemistry Tosylmethyl isocyanide
Zdroj:	Chemical and Pharmaceutical Bulletin. 27:2857-2861
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.27.2857
Popis:	The reaction of tosylmethyl isocyanide (7) with methyl propiolate (14a), dimethyl acetylenedicarboxylate (14b), methyl 3-(2-furoyl) propiolate (14c), and methyl 3-benzoylpropiolate (14d) in the presence of an equimolar amount of base at room temperature gave the corresponding 1 : 2 adducts, i.e., methyl 3-(1-pyrrolyl) acrylate derivatives (16a, 16b, 16c, and 16d, respectively) as final products. The temperature dependence of the reaction made it possible to isolate the pyrroles (15a and 15b), postulated as intermediates of the reaction, at low temperature.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::72f557246ae828be557bbd2c7c5a99cd https://doi.org/10.1248/cpb.27.2857 Zobrazit plný text záznamu