Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: IV. Cyclosulfenylation of 5-hexenoic acid amides and nucleophilic cleavage of reaction products

被引：0

作者：

Vas'kevich, A. I. ^{[1
]}

Tsizorik, N. M. ^{[1
]}

Staninets, V. I. ^{[1
]}

Vovk, M. V. ^{[1
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02094 Kiev, Ukraine

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 49卷 / 08期

关键词：

STEREOSELECTIVE-SYNTHESIS; INTERMEDIATE;

D O I：

10.1134/S1070428013080125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Anilides of 5-hexenoic acid react with arylsulfenyl chlorides in nitromethane in the presence of lithium perchlorate affording products of electrophilic cyclization, N-{6-[(arylsulfanyl)methyl]tetrahydro-2H-pyran-2-ylidene}anilinium perchlorates. The treatment of the latter with sodium acetate or secondary cycloalkylamines in the presence of water results in the opening of the tetrahydropyran ring and provides anilides or cycloalkylamides of 6-arylsulfanyl-5-hydroxyhexanoic acid.

引用

页码：1168 / 1174

页数：7

共 16 条

[1] Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: IV. Cyclosulfenylation of 5-hexenoic acid amides and nucleophilic cleavage of reaction products
A. I. Vas’kevich
N. M. Tsizorik
V. I. Staninets
M. V. Vovk
Russian Journal of Organic Chemistry, 2013, 49 : 1168 - 1174
[2] Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: V. Cyclization of anilides of styrylacetic acids in polyphosphoric acid
Vas'kevich, R. I.
Vas'kevich, A. I.
Daniluk, I. Yu.
Vovk, M. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (08) : 1175 - 1181
[3] Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: V. Cyclization of anilides of styrylacetic acids in polyphosphoric acid
R. I. Vas’kevich
A. I. Vas’kevich
I. Yu. Daniluk
M. V. Vovk
Russian Journal of Organic Chemistry, 2013, 49 : 1175 - 1181
[4] Intramolecular electrophilic cyclization of functional derivatives of unsaturated Compounds: I. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones from cinnamylacetamides and arylsulfenyl chlorides
A. I. Vas’kevich
N. M. Tsizorik
E. B. Rusanov
V. I. Stanitets
M. V. Vovk
Russian Journal of Organic Chemistry, 2011, 47 : 1146 - 1152
[5] Intramolecular electrophilic cyclization of functional derivatives of unsaturated Compounds: I. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones from cinnamylacetamides and arylsulfenyl chlorides
Vas'kevich, A. I.
Tsizorik, N. M.
Rusanov, E. B.
Stanitets, V. I.
Vovk, M. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (08) : 1146 - 1152
[6] Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: VIII. Cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides by the action of polyphosphoric acid and chlorosulfanylarenes
Danilyuk, I. Yu.
Vas'kevich, R. I.
Vas'kevich, A. I.
Vovk, M. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (07) : 987 - 992
[7] Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: VIII. Cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides by the action of polyphosphoric acid and chlorosulfanylarenes
I. Yu. Danilyuk
R. I. Vas’kevich
A. I. Vas’kevich
M. V. Vovk
Russian Journal of Organic Chemistry, 2016, 52 : 987 - 992
[8] Electrophilic intramolecular cyclization of functional dervatives of unsaturated compounds: VII. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones in the absence of salt additives and their selective reduction and oxidation
Tsizorik, N. M.
Vas'kevich, A. I.
Vas'kevich, R. I.
Vovk, M. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (02) : 226 - 230
[9] Electrophilic intramolecular cyclization of functional dervatives of unsaturated compounds: VII. Synthesis of 5-arylsulfanyl-6-phenylpiperidin-2-ones in the absence of salt additives and their selective reduction and oxidation
N. M. Tsizorik
A. I. Vas’kevich
R. I. Vas’kevich
M. V. Vovk
Russian Journal of Organic Chemistry, 2015, 51 : 226 - 230
[10] The conditions underlying the formation of unsaturated and cyclic compounds from halogenated open-chain derivatives. Part IV. Products formed from halogen derivatives of muconic acid. The constitution of muconic acid.
Chandrasena, JPC
Ingold, CK
JOURNAL OF THE CHEMICAL SOCIETY, 1922, 121 : 1306 - 1319

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