N-Acyl-1,2,3-triazoles - key intermediates in denitrogenative transformations

被引：6

作者：

Motornov, Vladimir ^{[1
]}

Pohl, Radek ^{[1
]}

Klepetarova, Blanka ^{[1
]}

Beier, Petr ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Flemingovo Nam 2, Prague 16610, Czech Republic

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 61期

关键词：

METAL-FREE SYNTHESIS; 1,2,3-TRIAZOLES; TRANSANNULATION; ALKYNES; NH-1,2,3-TRIAZOLES; REACTIVITY; TRIAZOLES; PYRROLES;

D O I：

10.1039/d3cc00987d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Elusive N-acyl-1,2,3-triazoles formed by direct acylation of NH-1,2,3-triazoles were isolated and fully characterized, including X-ray crystallography. A preference for the formation of thermodynamic N2 isomers was established. Direct evidence of interconversion between N1- and N2-acyltriazoles confirmed their value in denitrogenative transformations. Efficient synthesis of enamido triflates from NH-triazoles via the intermediacy of N2-acyl-1,2,3-triazoles was developed.

引用

页码：9364 / 9367

页数：4

共 50 条

[31] Base-Promoted Regiospecific Synthesis of Fully Substituted 1,2,3-Triazoles and 1,5-Disubstituted 1,2,3-Triazoles
Zhang, Xueying
Cui, Xue
Wang, Wei
Zeng, Tingting
Wang, Yan
Tan, Yinfeng
Liu, Dongyan
Wang, Xuesong
Li, Youbin
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (12) : 2176 - 2183
[32] Synthesis of Pyrazines from Rhodium-Catalyzed Reaction of 2H-Azirines with N-Sulfonyl 1,2,3-Triazoles
Ryu, Taekyu
Baek, Yonghyeon
Lee, Phil Ho
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (04) : 2376 - 2383
[33] Chiral Fused 1,2,3-Triazoles: A Synthetic Overview
Dhameja, Manoj
Kumar, Hariom
Gupta, Preeti
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (05) : 721 - 748
[34] An Overview of Synthetic Approaches towards 1,2,3-Triazoles
Rohila, Yajat
Sebastian, Sharol
Meenaskhi
Gupta, Manoj K.
SYNOPEN, 2024, 08 (01): : 58 - 62
[35] The banert cascade:: A synthetic sequence to polyfunctional NH-1,2,3-triazoles
Loren, JC
Sharpless, KB
SYNTHESIS-STUTTGART, 2005, Georg Thieme Verlag (09): : 1514 - 1520
[36] Regiospecific Aza-Michael Addition of 4-Aryl-1H-1,2,3-triazoles to Chalcones: Synthesis of 2,4-Disubstituted 1,2,3-Triazoles in Basic Medium
Bhagat, Ujjawal Kumar
Peddinti, Rama Krishna
SYNLETT, 2018, 29 (01) : 99 - 105
[37] DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles
Bhagat, Ujjawal Kumar
Kamaluddin
Peddinti, Rama Krishna
TETRAHEDRON LETTERS, 2017, 58 (04) : 298 - 301
[38] Transannulation of 1-Sulfonyl-1,2,3-triazoles with Heterocumulenes
Chuprakov, Stepan
Kwok, Sen Wai
Fokin, Valery V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) : 4652 - 4655
[39] Efficient Synthesis of 1-Sulfonyl-1,2,3-triazoles
Raushel, Jessica
Fokin, Valery V.
ORGANIC LETTERS, 2010, 12 (21) : 4952 - 4955
[40] Progresses in Syntheses and Applications of Bis-1,2,3-triazoles
Huo, Jingpei
Wei, Xinping
Mo, Guangzhen
Peng, Pai
Zhong, Mingli
Chen, Renhong
Wang, Zhaoyang
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (01) : 92 - 106

← 1 2 3 4 5 →