Synthesis of pyrrolidines and tetrahydro-1H-azepines from 4-aryl-1-benzoyl(ethoxycarbonyl)methyl-1-methyl-1,2,3,6-tetrahydropyridinium halides

被引：0

作者：

Soldatova S.A. ^{[1
]}

Gimranova G.S. ^{[1
]}

Mamyrbekova Zh.A. ^{[1
]}

Polyanskii K.B. ^{[1
]}

Akbulatov S.V. ^{[1
]}

Soldatenkov A.T. ^{[1
]}

机构：

[1] People's Friendship University of Russia

来源：

Chemistry of Heterocyclic Compounds | 2007年 / 43卷 / 11期

关键词：

1,2-shift; 4-aryl-1-benzoyl(ethoxycarbonyl)methyl-1,2,3,6-tetrahydropyridinium halides; N-ylides; Pyrollidines; Sigmatropic rearrangement; Tetrahydro-1H-azepines;

D O I：

10.1007/s10593-007-0219-2

中图分类号：

学科分类号：

摘要：

4-Aryl-1,2,3,6-tetrahydropyridinium quaternary salts which have a benzoylmethyl or ethoxycarbonylmethyl group on atom N-1 generate N-ylides when heated in the presence of NaH and they can rearrange in situ with contraction or expansion of the six-membered heterocycle to give substituted pyrrolidines (as a result of a [2,3]-sigmatropic rearrangement) or 1H-tetrahydroazepine derivatives (via Stevens rearrangement). The presence of an aryl substituent at position C-4 in the tetrahydropyridine ring allows to avoid the formation of elimination products and changes the direction of the reaction towards the preparation of the tetrahydroazepines. © 2007 Springer Science+Business Media, Inc.

引用

页码：1420 / 1425

页数：5

共 50 条

[1] Synthesis of pyrrolidines and tetrahydro-1H-azepines from 4-aryl-1-benzoyl(ethoxycarbonyl)methyl-1-methyl-1,2,3,6-tetrahydropyridinium halogenides
Soldatova, S. A.
Gimranova, G. S.
Mamyrbekova, Zh. A.
Polyanskii, K. B.
Akbulatov, S. V.
Soldatenkov, A. T.
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2007, (11): : 1670 - 1676
[2] UNEXPECTED COURSE FOR THE REACTION OF 1-DI(ETHOXYCARBONYL)METHYL-1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINIUM BROMIDE WITH DIMETHYL ACETYLENEDICARB-OXYLATE IN THE PRESENCE OF TRIETHYLAMINE
Soldatova, S. A.
Soldatenkov, A. T.
Suleimanov, R. R.
Kolyadina, N. M.
Khrustalev, V. N.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (11) : 1408 - 1409
[3] Rearrangements of N-Ylide Generated from 1-Ethoxycarbonylmethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinium Chloride
S. A. Soldatova
S. V. Akbulatov
G. S. Gimranova
Yu. O. Rudakov
K. B. Polyanskii
A. T. Soldatenkov
Chemistry of Heterocyclic Compounds, 2005, 41 (5) : 681 - 683
[4] Unexpected course for the reaction of 1-di(ethoxycarbonyl)methyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinium bromide with dimethyl acetylenedicarb-oxylate in the presence of triethylamine
S. A. Soldatova
A. T. Soldatenkov
R. R. Suleimanov
N. M. Kolyadina
V. N. Khrustalev
Chemistry of Heterocyclic Compounds, 2009, 45 : 1408 - 1409
[5] Synthesis of 1-aryl-2-methyl-3-ethoxycarbonyl-1,4,5,6-tetrahydro-4(1H)-pyridones and their derivatives
Mickevicius, V
Bylinskaite, J
TETRAHEDRON LETTERS, 1996, 37 (20) : 3489 - 3490
[6] Synthesis of 1-aryl-2-methyl-3-ethoxycarbonyl-1,4,5,6 - tetrahydro-4(1H)-pyridones and their derivatives
Mickevicius, V.
Bylinskaite, J.
Tetrahedron Letters, 37 (20):
[7] An improved synthesis of 1-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)ethanone, isoarecolone
Beach, JW
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (06) : 1861 - 1863
[8] An Improved Synthesis of 1-(1,2,3,6-Tetrahydro-1-methyl-4-pyridin yl)ethanone, Isoarecolone
Beach, J. W.
Journal of Heterocyclic Chemistry, 34 (06):
[9] 1,2,3,6-TETRAHYDRO-1-METHYL-4-(METHYLPYRROL-2-YL)PYRIDINE - STUDIES ON THE MECHANISM OF ACTION OF 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE
FINNEGAN, KT
IRWIN, I
DELANNEY, LE
RICAURTE, GA
LANGSTON, JW
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 1987, 242 (03): : 1144 - 1151
[10] Condensation Products of 1-Aryl-3-ethoxycarbonyl-2-methyl-1,4,5,6-tetrahydro-4(1H)pyridones with Hydrazine, Phenylhydrazine, and Hydroxylamine
R. Vaickelioniene
V. Mickevicius
G. Mikulskiene
Chemistry of Heterocyclic Compounds, 2004, 40 (6) : 767 - 775

← 1 2 3 4 5 →