Synthesis of Enaminones by Rhodium-Catalyzed Denitrogenative Rearrangement of 1-(N-Sulfonyl-1,2,3-triazol-4-yl)alkanols

被引：156

作者：

Miura, Tomoya ^{[1
]}

Funakoshi, Yuuta ^{[1
]}

Morimoto, Masao ^{[1
]}

Biyajima, Tsuneaki ^{[1
]}

Murakami, Masahiro ^{[1
]}

机构：

[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 42期

关键词：

ONE-POT SYNTHESIS; RING-EXPANSION; REGIOSELECTIVE SYNTHESIS; TRANSANNULATION; KETONES; 2-DIMETHYLAMINOMETHYLENE-1,3-DIONES; DINUCLEOPHILES; DERIVATIVES; REACTIVITY; MIGRATION;

D O I：

10.1021/ja308285r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enaminones are synthesized by the rhodium(II)-catalyzed denitrogenative rearrangement reaction of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols, which are readily prepared from propargylic alcohols and N-sulfonyl azides. Intramolecular 1,2-hydride (or -alkyl) migration occurs with an intermediary alpha-imino rhodium-(II) carbenoid species generated through denitrogenation of the 1,2,3-triazol-4-yl moiety. The resulting enaminones is converted into various heterocycles with replacement of the N-sulfonyl group.

引用

收藏

页码：17440 / 17443

页数：4

相关论文

共 63 条

[31] Ni(OAc)2: a highly efficient catalyst for the synthesis of enaminone and enamino ester derivatives under solvent-free conditions [J].

Liu, Ju-Yan ;

Cao, Gai-E ;

Xu, Wei ;

Cao, Jie ;

Wang, Wei-Lu .

APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (10) :685-691

[32] Ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes via a N-sulfonyl-1,2,3-triazole intermediate [J].

Liu, Renhe ;

Zhang, Min ;

Winston-McPherson, Gabrielle ;

Tang, Weiping .

CHEMICAL COMMUNICATIONS, 2013, 49 (39) :4376-4378

[33] Highly controlling selectivity of copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) between sulfonyl azids and normal alkynes or propynoates [J].

Liu, Yantao ;

Wang, Xinyan ;

Xu, Jimin ;

Zhang, Qun ;

Zhao, Yi ;

Hu, Yuefei .

TETRAHEDRON, 2011, 67 (34) :6294-6299

[34] Concise Synthesis of Bicyclic Pyridinol Antioxidants [J].

Lu, Jun ;

Cai, Xiaoqing ;

Hecht, Sidney M. .

ORGANIC LETTERS, 2010, 12 (22) :5189-5191

[35] Gold(I)-catalyzed ring expansion of cyclopropanols and cyclobutanols [J].

Markham, JP ;

Staben, ST ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) :9708-9709

[36] REACTION OF 2-DIMETHYLAMINOMETHYLENE-1,3-DIONES WITH DINUCLEOPHILES .6. SYNTHESIS OF ETHYL OR METHYL 1,5-DISUBSTITUTED H-1-PYRAZOLE-4-CARBOXYLATES [J].

MENOZZI, G ;

MOSTI, L ;

SCHENONE, P .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) :1669-1675

[37] Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles [J].

Miura, Tomoya ;

Biyajima, Tsuneaki ;

Fujii, Tetsuji ;

Murakami, Masahiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :194-196

[38] Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles [J].

Miura, Tomoya ;

Yamauchi, Motoshi ;

Murakami, Masahiro .

CHEMICAL COMMUNICATIONS, 2009, (12) :1470-1471

[39]

NAGAO K, 1983, SYNTHESIS-STUTTGART, P197

[40] Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds [J].

Negri, G ;

Kascheres, C ;

Kascheres, AJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 41 (04) :461-491

← 1 2 3 4 5 6 7 →