CH3CO2H-prompted three components tandem reaction: An efficient and practical approach to trisubstituted pyrrolo[1,2-a]pyrazines

被引：9

作者：

Chu, Xianglong ^{[1
]}

Zhang, Zeyuan ^{[1
]}

Wang, Congcong ^{[1
]}

Chen, Xuan ^{[1
]}

Wang, Bin ^{[1
]}

Ma, Chen ^{[1
,2
,3
]}

机构：

[1] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Shandong, Peoples R China

[2] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China

[3] Peking Union Med Coll, Beijing 100050, Peoples R China

来源：

TETRAHEDRON | 2017年 / 73卷 / 51期

基金：

美国国家科学基金会;

关键词：

Metal-free; Pyrrolo[1,2-a]pyrazines; Cascade reaction; BIOLOGICAL EVALUATION; 7-AZAINDOLIZINES; AZAINDOLIZINES; DERIVATIVES; INHIBITORS; PYRROLES; AGENTS; AKT;

D O I：

10.1016/j.tet.2017.10.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient protocol for the synthesis of trisubstitued pyrrolo[1,2-a]pyrazines through three components cyclization and one-pot cascade reaction is presented. Various trisubstitued pyrrolo[1,2-a]pyrazines are obtained by this metal-free process in moderate to good yields. (C) 2017 Published by Elsevier Ltd.

引用

页码：7185 / 7189

页数：5

共 18 条

[1] Pyrrolo[1,2-a]pyrazine and pyrazolo[1,5-a]pyrazine: Novel, potent, and selective series of Vasopressin1b receptor antagonists [J].

Arban, Roberto ;

Bianchi, Federica ;

Buson, Alberto ;

Cremonesi, Susanna ;

Di Fabio, Romano ;

Gentile, Gabriella ;

Micheli, Fabrizio ;

Pasquarello, Alessandra ;

Pozzan, Alfonso ;

Tarsi, Luca ;

Terreni, Silvia ;

Tonelli, Federica .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (17) :5044-5049

[2]

ARTICO M, 1983, SYNTHESIS-STUTTGART, P931

[3]

BUCHAN R, 1985, J ORG CHEM, V50, P1324, DOI 10.1021/jo00208a042

[4] AZAINDOLIZINES .7. 7-AZAINDOLIZINES, THEIR REACTIVITY AND REACTION WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].

BUCHAN, R ;

FRASER, M ;

LIN, PVSKT .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1074-1076

[5] A NEW APPROACH FOR THE SYNTHESIS OF FUSED PYRROLES - THE SYNTHESIS OF ACYL SUBSTITUTED PYRROLO[1,2-X]AZINES [J].

COPAR, A ;

STANOVNIK, B ;

TISLER, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (06) :1577-1579

[6]

Desplat V, 2008, J ENZYM INHIB MED CH, V23, P648, DOI [10.1080/14756360802205448, 10.1080/14756360802205448 ]

[7] Synthesis of substituted 7,8-di(propylsulfonyl)pyrrolo[1,2-a]pyrazines [J].

Dontsova, N. E. ;

Shestopalov, A. M. ;

Litvinov, V. P. .

RUSSIAN CHEMICAL BULLETIN, 2008, 57 (02) :434-436

[8] Diverse Heterocyclic Scaffolds as Allosteric Inhibitors of AKT [J].

Kettle, Jason G. ;

Brown, Simon ;

Crafter, Claire ;

Davies, Barry R. ;

Dudley, Phillippa ;

Fairley, Gary ;

Faulder, Paul ;

Fillery, Shaun ;

Greenwood, Hannah ;

Hawkins, Janet ;

James, Michael ;

Johnson, Keith ;

Lane, Clare D. ;

Pass, Martin ;

Pink, Jennifer H. ;

Plant, Helen ;

Cosulich, Sabina C. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (03) :1261-1273

[9] Synthesis and biological evaluation of 1,2-dithiol-3-thiones and pyrrolo[1,2-a]pyrazines as novel hypoxia inducible factor-1 (HIF-1) inhibitor [J].

Lee, Young Hun ;

Lee, Jung Min ;

Kim, Sang Geon ;

Lee, Yong Sup .

BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (12) :2843-2851

[10] Multicomponent Reactions of Aldo-X Bifunctional Reagent -Oxoketene Dithioacetals and Indoles or Amines: Divergent Synthesis of Dihydrocoumarins, Quinolines, Furans, and Pyrroles [J].

Liu, Changhui ;

Zhou, Li ;

Jiang, Dan ;

Gu, Yanlong .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (03) :367-372

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