Reactions of enamino keto esters of 1,2,3,4-tetrahydroisoquinoline series with nucleophiles

被引：0

作者：

O. V. Surikova

A. G. Mikhailovskii

M. I. Vakhrin

机构：

[1] Perm State Pharmaceutical Academy,

来源：

Chemistry of Heterocyclic Compounds | 2010年 / 46卷

关键词：

3,3-dimethyl-1-(5-thioxo-1,5-dihydro-1,2,4-triazol-3-ylmethylidenecarbonyl)-1,2,3,4-tetra-hydroisoquinoline; methyl ester of 3-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-idene)pyruvic acid; nitrile of 2-cyano-4-dicyanomethylidene-5-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-idene)-3-oxo-pentanoic acid; semicarbazide; thiosemicarbazide; annelation of the pyrrole ring; heterocyclization; ester condensation with malonodinitrile;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

It has been shown that the reaction of the methyl ester of 3-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-idene)pyruvic acid with thiosemicarbazide in glacial acetic acid leads to heterocyclization with the formation of 3,3-dimethyl-1-(5-thioxo-1,5-dihydro-1,2,4-triazol-3-ylmethylidenecarbonyl)-1,2,3,4-tetra-hydroisoquinoline, but the interaction with semicarbazide under the same conditions leads to annelation of the pyrrole ring. On condensation of the enamino keto ester with malonodinitrile, the nitrile of 2-cyano-4-dicyanomethylidene-5-(3,3-dimethyl-1,2,3.4-tetrahydroisoquinolin-1-idene)-3-oxo-pentanoic acid is formed.

引用

页码：179 / 183

页数：4

共 40 条

[1] Reactions of enamino keto esters of 1,2,3,4-tetrahydroisoquinoline series with nucleophiles
Surikova, O. V.
Mikhailovskii, A. G.
Vakhrin, M. I.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (02) : 179 - 183
[2] Reactions of 2,3-dioxopyrrolo[2,1-a]isoquinolinecarboxylic acid esters and amides with nitrogen-centered nucleophiles
O. V. Surikova
A. G. Mikhailovskii
N. N. Polygalova
M. I. Vakhrin
Russian Journal of Organic Chemistry, 2008, 44 : 840 - 844
[3] [3 + 3] Cyclocondensation of 1-alkyl- 3,4 dihydroisoquinolines with β-keto esters. new annelation reaction in a series of cyclic schiff’s bases
O. V. Gulyakevich
A. A. Govorova
P. V. Kurman
A. S. Lyakhov
A. L. Mikhal’chuk
Chemistry of Heterocyclic Compounds, 2004, 40 (10) : 1288 - 1294
[4] [3 + 3] Cyclocondensation of 1-alkyl-3,4-dihydroisoquinolines with β-keto esters. New annelation reaction in a series of cyclic Schiff's bases
Gulyakevich O.V.
Govorova A.A.
Kurman P.V.
Lyakhov A.S.
Mikhal'chuk A.L.
Chemistry of Heterocyclic Compounds, 2004, 40 (10) : 1288 - 1294
[5] Synthesis and reactions with N-nucleophiles of 1-(thien-2-yl)- and 1-(4-hydroxyphenyl)-3,4,4-trichloro-3-buten-1-ones
V. I. Potkin
S. K. Petkevich
P. V. Kurman
Russian Journal of Organic Chemistry, 2010, 46 : 1305 - 1312
[6] Synthesis and reactions with N-nucleophiles of 1-(thien-2-yl)- and 1-(4-hydroxyphenyl)-3,4,4-trichloro-3-buten-1-ones
Potkin, V. I.
Petkevich, S. K.
Kurman, P. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (09) : 1305 - 1312
[7] Docking Study, Synthesis, Characterization and Preliminary Cytotoxic Evaluation of new 1,2,3,4-Tetrahydroppyrimidine Derivatives
Mohammed, Noor M.
JOURNAL OF CONTEMPORARY MEDICAL SCIENCES, 2022, 8 (05): : 329 - 336
[8] Reaction of α-iminomethylene amino esters with mono- and bidentate nucleophiles:: a straightforward route to 2-amino-1H-5-imidazolones
Heras, M
Ventura, M
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Villalgordo, JM
TETRAHEDRON, 2001, 57 (20) : 4371 - 4388
[9] Synthesis of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones by the Condensation of 3-Alkylamino-5-amino-1-phenyl[1,2,4]triazoles with β-Keto Esters or Diethyl Ethoxymethylenemalonate
Astakhov, A. V.
Zubatyuk, R. I.
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Chernyshev, V. M.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 49 (10) : 1500 - 1507
[10] Synthesis of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones by the Condensation of 3-Alkylamino-5-amino-1-phenyl[1,2,4]triazoles with β-Keto Esters or Diethyl Ethoxymethylenemalonate
A. V. Astakhov
R. I. Zubatyuk
R. S. Abagyan
V. M. Chernyshev
Chemistry of Heterocyclic Compounds, 2014, 49 : 1500 - 1507

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