1973
DOI: 10.1002/cber.19731061022
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Synthesen mit α‐metallierten Isocyaniden, XXV. 4‐Cyan‐2‐isocyanalkansäure‐äthylester, 4‐Cyan‐2‐(formylamino)alkansäure‐äthylester und 4‐Cyan‐5(4)‐pyrrolin‐2‐carbonsäure‐äthylester aus α‐metallierten Isocyanalkansäure‐äthylestern und Acrylnitrilen

Abstract: Synthesen mit a-metallierten Isocyaniden, XXV 1) 4-Cyan-2-isocyanalkansaure-athylester, 4-Cyan-2-(formylamino)alkansaure-athylester und 4-Cyan-5(4)-pyrrolin-2-carbons~ure-athylester aus a-metallierten Isocyanalkansaure-athylestern und Acrylnitrilen Eingegangen atn 2. Mat 1973 4-Cyan-2-isocyanalkans8ure-~thylester (7, 8, 9) cntstehen aus Acrylnitrilen 5 und Tsocyan-essigs8iure-athylesler bzw. -propionsuure-uthylester (1 bzw. 2) in Athaiiol in Gegenwart katalytischer Mengen Natriumathylat bei ca. 30'C. Mit Salzs… Show more

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Cited by 25 publications
(2 citation statements)
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“…Thus, when R . 252 The β-substituted Michael adducts 498 containing an R-hydrogen atom undergo thermal cyclization under basic conditions via the ester enolate 499 to give 5-alkoxyoxazoles 500 bearing an ester group (X ) COOEt) 250 or a cyano group (X ) CN) 251 in moderate yields (Scheme 127).…”
Section: Reactions With Sulfur Electrophilesmentioning
confidence: 99%
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“…Thus, when R . 252 The β-substituted Michael adducts 498 containing an R-hydrogen atom undergo thermal cyclization under basic conditions via the ester enolate 499 to give 5-alkoxyoxazoles 500 bearing an ester group (X ) COOEt) 250 or a cyano group (X ) CN) 251 in moderate yields (Scheme 127).…”
Section: Reactions With Sulfur Electrophilesmentioning
confidence: 99%
“…The combination of a Michael addition with a subsequent thermal cyclization via insertion of an isocyanide into the activated C−H bond leads to a variety of heterocyclic compounds. Thus, monoadducts of type 492 , which can be generated in situ or obtained after isolation, can be cyclized to 1- and 2-pyrrolines 493 or 494 by heating with sodium ethoxide at 70−110 °C, thanks to the stabilization of the generated carbanion α to the electron-withdrawing X group. The cyclization also takes place efficiently in the presence of catalytic amounts of Cu 2 O . The position of the double bond (formation of 1- or 2-pyrrolines) is determined by the structure of the starting adduct.…”
Section: α-Isocyanoacetates As a Michael Donorsmentioning
confidence: 99%