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

• Published in: Russian journal of organic chemistry Vol. 48; no. 2; pp. 193 - 201
• Main Authors: Vas’kevich, A. I., Tsizorik, N. M., Rusanov, E. B., Staninets, V. I., Vovk, M. V.
• Format: Journal Article
• Language: English
• Published: Dordrecht SP MAIK Nauka/Interperiodica 01-02-2012
• Subjects: Chemistry; Chemistry and Materials Science; Organic Chemistry; Dihydrofuran; Perchlorate; Sulfanyl; Oily Substance; Lithium Perchlorate
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428012020078

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
-{(2
Z
)-5-[(arylsulfanyl)methyl] dihydrofuran-2(3
H
)-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.