A convenient synthesis of 1-acyl indolizines by 1,3-dipolar cycloaddition reactions of pyridinium ylides and alpha,beta-unsaturated aldehydes or ketones in the presence of tetrakis-pyridine cobalt dichromate

被引：23

作者：

Zhang, XC ^{[1
]}

Cao, WL ^{[1
]}

Wei, XD ^{[1
]}

Hu, HW ^{[1
]}

机构：

[1] NANJING UNIV,DEPT CHEM,NANJING 210093,PEOPLES R CHINA

来源：

SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 08期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1080/00397919708006070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of tetrakispyridine cobalt dichromate (CoPy(4)(HCrO4)(2)), pyridinium ylides and alpha,beta-unsaturated aldehydes or ketones undergo 1,3-dipolar cycloaddition reactions followed by in situ aromatization to give 1-acyl substituted indolizines in moderate to good yields.

引用

页码：1395 / 1403

页数：9

共 44 条

[31] Diastereoselective synthesis of diverse 3,2′-pyrrolidinyl bispirooxindoles via 1,3-dipolar cycloaddition reactions of azomethine ylides with exocyclic α,β-unsaturated ketones and in silico studies for prediction of bioactivity
Dutta, Kartik
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[32] REACTION OF ALDEHYDES WITH 1,3-DICARBONYL COMPOUNDS IN THE PRESENCE OF POTASSIUM CARBONATE - CONVENIENT SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS VIA DEACYLATION
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CHEMISTRY LETTERS, 1978, (12) : 1325 - 1328
[33] The first approach to the synthesis of 1-unsubstituted 2-arylindolizines by intramolecular 1,5-dipolar cyclization of 2-(2-arylethenyl)pyridinium ylides in the presence of tetrakis(pyridine)cobalt (II) dichromate
Zhou, J
Hu, YF
Hu, HW
SYNTHESIS-STUTTGART, 1999, (01): : 166 - 170
[34] Iodine-mediated sp3 C-H functionalization of methyl ketones: a one-pot synthesis of functionalized indolizines via the 1,3-dipolar cycloaddition reaction between pyridinium ylides and ynones
Yavari, Issa
Sheykhahmadi, Jamil
Naeimabadi, Maryam
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MOLECULAR DIVERSITY, 2017, 21 (01) : 1 - 8
[35] Asymmetric 1,3-dipolar cycloaddition of optically active trifluoromethylated alpha,beta-unsaturated aryl sulfones with nitrones: The use of o-dialkylaminoethyl chiral auxiliaries
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Okano, T
Eguchi, S
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JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (10): : 1581 - 1586
[36] Preparation of indolizine-3-carboxamides and indolizine-3-carbonitriles by 1,3-dipolar cycloaddition of N-(cyanomethyl)pyridinium ylides to alkenes in the presence of tetrakispyridinecobalt(II) dichromate or manganese(IV) oxide
Wang, BX
Zhang, XC
Li, J
Jiang, X
Hu, YF
Hu, HW
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11): : 1571 - 1575
[37] 1,3-DIPOLAR CHARACTER OF 6-MEMBERED HETEROAROMATIC RINGS .47. BETAINES DERIVED FROM 3-HYDROXYPYRIDINE AND BETA-CHLORO-ALPHA,BETA-UNSATURATED KETONES
KATRITZKY, AR
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BAYYUK, S
BOLOURI, AMA
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POLISH JOURNAL OF CHEMISTRY, 1978, 53 (01) : 57 - 72
[38] Catalytic enantioselective tandem carbonyl ylide formation/1,3-dipolar cycloaddition reactions of α-diazo ketones with aromatic aldehydes using dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-valinate]
Tsutsui, Hideyuki
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Abe, Takumi
Anada, Masahiro
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ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (4-5) : 521 - 526
[39] 4-(N,N-Dimethylamino)pyridine (DMAP)-Catalyzed 1,3-Dipolar Cycloaddition of 3-Aminooxindole-Based Azomethine Ylides with ,-Unsaturated Acyl Phosphonates for the Construction of Spiropyrrolidinyl-2,3-oxindoles
He, Jin
Sun, Rong-Guo
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Chen, Lin
SYNTHESIS-STUTTGART, 2019, 51 (06): : 1353 - 1364
[40] Diverse cycloaddition chemistry leading to overall Michael addition in the reactions of 1,1-bis(dimethylamino)-2,2-difluoroethene with alpha,beta-unsaturated aldehydes, ketones, esters, and nitriles
Xu, YL
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JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19): : 6503 - 6506

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