Unexpected Synthesis of N-Acyl Indolines via a Consecutive Cyclization of Iminophosphorane

被引：12

作者：

Li, Wen-Jing ^{[1
]}

Zhao, Fen-Fen ^{[1
]}

Ding, Ming-Wu ^{[1
]}

机构：

[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China

来源：

SYNLETT | 2011年 / 02期

基金：

中国国家自然科学基金;

关键词：

N-acyl indoline; iminophosphorane; cyclization; Staudinger reaction; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; INDOLES; ROUTE; AMINATION; STRATEGY;

D O I：

10.1055/s-0030-1259280

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Acyl indolines were obtained unexpectedly from a consecutive cyclization of iminophosphorane in refluxing xylene or 1,2-dichlorobenzene in good yields. This new approach provides an efficient and direct access to the biologically important indolines which are further oxidizable to indoles and oxindoles.

引用

页码：265 / 267

页数：3

共 34 条

[1] 5-HYDROXYTRYPTAMINE (5-HT3) RECEPTOR ANTAGONISTS .2. 1-INDOLINECARBOXAMIDES [J].

BERMUDEZ, J ;

DABBS, S ;

JOINER, KA ;

KING, FD .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (07) :1929-1932

[2] CC-1065 and the duocarmycins: Synthetic studies [J].

Boger, DL ;

Boyce, CW ;

Garbaccio, RM ;

Goldberg, JA .

CHEMICAL REVIEWS, 1997, 97 (03) :787-828

[3] A Cascade Approach to Pyridines from 2-Azido-2,4-dienoates and α-Diazocarbonyl Compounds [J].

Chen, Zheng-Bo ;

Hong, Deng ;

Wang, Yan-Guang .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) :903-905

[4] Facile Preparation of 3-Substituted Benzisothiazoles from o-Mercaptoacylphenones [J].

Devarie-Baez, Nelmi O. ;

Xian, Ming .

ORGANIC LETTERS, 2010, 12 (04) :752-754

[5] Synthesis of highly substituted indolines and indoles via intramolecular [4+2] cycloaddition of ynamides and conjugated enynes [J].

Dunetz, JR ;

Danheiser, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5776-5777

[6] A domino amidation route to indolines and indoles: Rapid syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine [J].

Ganton, MD ;

Kerr, MA .

ORGANIC LETTERS, 2005, 7 (21) :4777-4779

[7] Enantioselective synthesis of 3-substituted indolines by asymmetric intramolecular carbolithiation in the presence of (-)-sparteine [J].

Gil, GS ;

Groth, UM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) :6789-6790

[8] CENTRAL SEROTONIN RECEPTORS AS TARGETS FOR DRUG RESEARCH [J].

GLENNON, RA .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (01) :1-12

[9] Unexpected Synthesis of Rearranged 3,4-Dihydroquinazolines by a Sequential Ugi 4CC/Aza-Wittig/Carbodiimide-Mediated Cyclization [J].

He, Ping ;

Wu, Jing ;

Nie, Yi-Bo ;

Ding, Ming-Wu .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (06) :1088-1095

[10] New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence [J].

He, Ping ;

Wu, Jing ;

Nie, Yi-Bo ;

Ding, Ming-Wu .

TETRAHEDRON, 2009, 65 (41) :8563-8570

← 1 2 3 4 →