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 50 条

[41] Synthesis and characterization of novel N-acyl cyclic urea derivatives
Yang, Tingting
Gao, Guohua
ARKIVOC, 2012, : 304 - 316
[42] The synthesis and antiproliferative activity of a new N-acyl derivative of doxorubicin
Shcherbakov, VM
Devichenskii, VM
Vorontsov, EA
Kuznetsov, SL
Kryukov, LN
BIOORGANICHESKAYA KHIMIYA, 1999, 25 (03): : 226 - 229
[43] SYNTHESIS OF N-ACYL AMINO-ACIDS BY A CARBONYLATION REACTION
WAKAMATSU, H
UDA, J
YAMAKAMI, N
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (23): : 1540 - +
[44] Synthesis, surface and biological properties of sodium N-acyl isoleucines
Sreenu, Madhumanchi
Rao, Bhamidipati V. S. K.
Prasad, Rachapudi Badari Narayana
Sujitha, Pombala
Chityala, Ganesh Kumar
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2014, 116 (02) : 193 - 206
[45] Solid-phase synthesis of indolines via palladium-catalyzed cyclization
Yu, YP
Ostresh, JM
Houghten, RA
TETRAHEDRON LETTERS, 2003, 44 (12) : 2569 - 2572
[46] SYNTHESIS OF N-ACYL AROMATIC ALPHA-AMINO-ACIDS
KU, B
OH, DY
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1988, 9 (04) : 255 - 255
[47] Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction
Minatti, Ana
Buchwald, Stephen L.
ORGANIC LETTERS, 2008, 10 (13) : 2721 - 2724
[48] ELECTROCHEMICAL SYNTHESIS OF SEMICYCLIC AND CYCLIC N-ACYL N,O-ACETALS
IWASAKI, T
HORIKAWA, H
MATSUMOTO, K
MIYOSHI, M
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09): : 1552 - 1554
[49] Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols
Ziqian Bai
Shiyang Zhu
Yiyao Hu
Peng Yang
Xin Chu
Gang He
Hao Wang
Gong Chen
Nature Communications, 13
[50] ELECTROCHEMICAL SYNTHESIS OF THE VINYLOGS OF N-ACYL N,O-ACETALS AND THEIR REACTIVITY
FASSEUR, D
RIGO, B
CAULIEZ, P
DEBACKER, M
COUTURIER, D
TETRAHEDRON LETTERS, 1990, 31 (12) : 1713 - 1716

← 1 2 3 4 5 →