Intramolecular electrophilic cyclization of functional derivatives of unsaturated compounds: II. Synthesis and transformation of N-{(2Z)-5-[(arylsulfanyl)methyl]dihydrofuran-2(3H)-ylidene}-N-alkyl(aryl)aminium perchlorates View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2012-02

AUTHORS

A. I. Vas’kevich, N. M. Tsizorik, E. B. Rusanov, V. I. Staninets, M. V. Vovk

ABSTRACT

N-Alkyl(aryl)amides of allylacetic acid when reacting with arylsulfenyl chlorides in acetic acid in the presence of lithium perchlorate undergo a selective cyclization to form N-{(2Z)-5-[(arylsulfanyl)methyl] dihydrofuran-2(3H)-ylidene}-N-alkyl-(aryl)aminium perchlorates. Treating of the latter with sodium acetate leads to the formation of the corresponding 5-[(arylsulfanyl)methyl]lactones, and with sodium ethylate, to 5-[(arylsulfanyl) methyl]-2-iminolactones. In reaction with secondary cycloalkylamines in the presence of water a transamidation and tetrahydrofuran ring opening occurs to afford 5-arylsulfanyl-4-hydroxypentanoic acid amides. More... »

PAGES

193-201

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428012020078

DOI

http://dx.doi.org/10.1134/s1070428012020078

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1004271175


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