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

被引：154

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

页码：17440 / 17443

页数：4

共 50 条

[31] [1-(3-Chlorophenyl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate
Boechat, Nuebia
Ferreira, Maria de Lourdes G.
Bastos, Monica M.
Wardell, James L.
Wardell, Solange M. S. V.
Tiekink, Edward R. T.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2934 - U495
[32] (1,2,3-Triazol-4-yl)benzenamines: Synthesis and activity against VEGF receptors 1 and 2
Kiselyov, Alexander S.
Semenova, Marina
Semenov, Victor V.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (05) : 1344 - 1348
[33] Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with N-Sulfonyl 1,2,3-Triazoles
Chuprakov, Stepan
Kwok, Sen Wai
Zhang, Li
Lercher, Lukas
Fokin, Valery V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (50) : 18034 - +
[34] Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles
Chuprakov, Stepan
Kwok, Sen Wai
Zhang, Li
Lercher, Lukas
Fokin, Valery V.
Journal of the American Chemical Society, 2009, 131 (50): : 18034 - 18035
[35] Rhodium Catalyzed Synthesis of Benzopyrans via Transannulation of N-Sulfonyl-1,2,3-triazoles with 2-Hydroxybenzyl Alcohols
Yadagiri, Dongari
Chaitanya, Manthena
Reddy, Angula Chandra Shekar
Anbarasan, Pazhamalai
ORGANIC LETTERS, 2018, 20 (13) : 3762 - 3765
[36] Synthesis of 1-(3-(1-substituted-1,2,3-triazol-4-yl)-1,2,4-triazol-5-yl)-tetrazoles by Sequential Assembly of Azole Fragments
Zviagin, Eugene
Saraev, Vyacheslav
Sysoiev, Dmytro
Klepetarova, Blanka
Mazur, Maryna
Zhelavskyi, Oleksii
Shliapkina, Yuliia
Mueller, Thomas J. J.
Chebanov, Valentyn
CHEMISTRYSELECT, 2021, 6 (45): : 12890 - 12894
[37] Rhodium-catalyzed denitrogenative transannulation of 1,2,3-triazolyl-carbamates: efficient access to 4-aminooxazolidinones
Pal, Kuntal
Volla, Chandra M. R.
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1380 - 1384
[38] Synthesis of Polysubstituted Furans via Rh(II)-Catalyzed [2+3] Annulation of N-Sulfonyl-1,2,3-triazoles with Enaminones
Lei, Xiaoqiang
Feng, Juan
Guo, Qinglan
Li, Yuanhe
Shi, Jiangong
ORGANIC LETTERS, 2023, 25 (40) : 7338 - 7343
[39] Di-tert-butyl N-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl] methyl}iminodiacetate
Francois, Alison
Marty, Louise
Picard, Claude
Mallet-Ladeira, Sonia
Benoist, Eric
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3162 - +
[40] Synthesis of New Symmetrical N, N′-Diacylhydrazines and 2-(1,2,3-Triazol-4-yl)-1,3,4-oxadiazoles
Abdel-Wahab, Bakr F.
Alotaibi, Mohammad Hayal
El-Hiti, Gamal A.
LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (08) : 591 - 596

← 1 2 3 4 5 →