Rhodium-catalyzed tandem C-H activation and aza-Michael addition of 2-arylquinazolin-4-ones with acrylates for the synthesis of pyrrolo[2,1-b]quinazolin-9(1H)-one derivatives

被引：31

作者：

Jiang, Xin ^{[1
,2
]}

Yang, Qin ^{[1
,2
]}

Yuan, Jianjun ^{[1
,2
]}

Deng, Zhihong ^{[1
,2
]}

Mao, Xuechun ^{[1
,2
]}

Peng, Yiyuan ^{[1
,2
]}

Yu, Chuyi ^{[3
]}

机构：

[1] Minist Educ, Jiangxi Provinces Key Lab Green Chem, Key Lab Funct Small Organ Mol, Nanchang 330022, Peoples R China

[2] Jiangxi Normal Univ, Nanchang 330022, Peoples R China

[3] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 330022, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 09期

基金：

中国国家自然科学基金;

关键词：

Rhodium catalysis; C-H activation; Aza-Michael addition; Quinazolin-4-one; Pyrrolo[2,1-b]quinazolin-9(1H)-one; Tandem reaction; DIELS-ALDER REACTION; BOND FORMATION; QUINAZOLINE; QUINOLINE;

D O I：

10.1016/j.tet.2016.01.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, a rhodium-catalyzed reaction of 2-arylquinazolin-4-ones with acrylates is described, leading to pyrrolo[2, 1-b]quinazolin-9(1H)-one derivatives with high efficiency and good tolerance of functional groups. In the reactions, it is believed that tandem C-H activation and aza-Michael addition are involved. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：1238 / 1243

页数：6

共 40 条

[1] CHOLECYSTOKININ ANTAGONISTS - SYNTHESIS OF ASPERLICIN ANALOGS WITH IMPROVED POTENCY AND WATER SOLUBILITY [J].

BOCK, MG ;

DIPARDO, RM ;

RITTLE, KE ;

EVANS, BE ;

FREIDINGER, RM ;

VEBER, DF ;

CHANG, RSL ;

CHEN, TB ;

KEEGAN, ME ;

LOTTI, VJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (10) :1941-1945

[2]

Brown D. J., 1996, CHEM HETEROCYCLIC CO, V1

[3] A POTENT NONPEPTIDE CHOLECYSTOKININ ANTAGONIST SELECTIVE FOR PERIPHERAL-TISSUES ISOLATED FROM ASPERGILLUS-ALLIACEUS [J].

CHANG, RSL ;

LOTTI, VJ ;

MONAGHAN, RL ;

BIRNBAUM, J ;

STAPLEY, EO ;

GOETZ, MA ;

ALBERSSCHONBERG, G ;

PATCHETT, AA ;

LIESCH, JM ;

HENSENS, OD ;

SPRINGER, JP .

SCIENCE, 1985, 230 (4722) :177-179

[4] Synthesis of quinazolinones and quinazolines [J].

Connolly, DJ ;

Cusack, D ;

O'Sullivan, TP ;

Guiry, PJ .

TETRAHEDRON, 2005, 61 (43) :10153-10202

[5] DESIGN OF NONPEPTIDAL LIGANDS FOR A PEPTIDE RECEPTOR - CHOLECYSTOKININ ANTAGONISTS [J].

EVANS, BE ;

RITTLE, KE ;

BOCK, MG ;

DIPARDO, RM ;

FREIDINGER, RM ;

WHITTER, WL ;

GOULD, NP ;

LUNDELL, GF ;

HOMNICK, CF ;

VEBER, DF ;

ANDERSON, PS ;

CHANG, RSL ;

LOTTI, VJ ;

CERINO, DJ ;

CHEN, TB ;

KING, PJ ;

KUNKEL, KA ;

SPRINGER, JP ;

HIRSHFIELD, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (07) :1229-1239

[6] ASPERLICIN, A NOVEL NON-PEPTIDAL CHOLECYSTOKININ ANTAGONIST FROM ASPERGILLUS-ALLIACEUS - FERMENTATION, ISOLATION AND BIOLOGICAL PROPERTIES [J].

GOETZ, MA ;

LOPEZ, M ;

MONAGHAN, RL ;

CHANG, RSL ;

LOTTI, VJ ;

CHEN, TB .

JOURNAL OF ANTIBIOTICS, 1985, 38 (12) :1633-1637

[7] Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives [J].

Ju, Yi ;

Liu, Feng ;

Li, Chaozhong .

ORGANIC LETTERS, 2009, 11 (16) :3582-3585

[8] ASPERLICIN, A NOVEL NON-PEPTIDAL CHOLECYSTOKININ ANTAGONIST FROM ASPERGILLUS-ALLIACEUS - STRUCTURE ELUCIDATION [J].

LIESCH, JM ;

HENSENS, OD ;

SPRINGER, JP ;

CHANG, RSL ;

LOTTI, VJ .

JOURNAL OF ANTIBIOTICS, 1985, 38 (12) :1638-1642

[9] Cross-coupling/annulations of quinazolones with alkynes for access to fused polycyclic heteroarenes under mild conditions [J].

Lu, Hui ;

Yang, Qin ;

Zhou, Yirong ;

Guo, Yanqin ;

Deng, Zhihong ;

Ding, Qiuping ;

Peng, Yiyuan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (05) :758-764

[10]

Ma ZZ, 1997, HETEROCYCLES, V46, P541

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