Rhodium-Catalyzed [4+2]-Annulation of o-Acylanilines with N-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines

被引：4

作者：

Rupa, Kavuri ^{[1
]}

Yadagiri, Dongari ^{[1
,2
]}

Anbarasan, Pazhamalai ^{[1
]}

机构：

[1] Indian Inst Technol Madras, Dept Chem, Chennai 600036, India

[2] Indian Inst Technol Roorkee, Dept Chem, Roorkee 247667, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 13期

关键词：

QUINOLINE; TRANSANNULATION; REARRANGEMENT; CHEMOSENSOR; ALKYLATION; INDOLINES; ALCOHOLS; COMPLEX; ACCESS;

D O I：

10.1021/acs.joc.3c00748

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient synthesis of 3-aminoquinolines has been demonstratedfrom readily accessible N-sulfonyl-1,2,3-triazolesand o-acylaniline derivatives. This transformationinvolves the generation of C-C and C-N bonds throughinsertion of rhodium azavinyl carbenoid into a N-H bond followedby cyclization and aromatization. The important features include goodfunctional group tolerance, synthesis of indoloquinoline, and isolationof N-H-inserted product, a potential intermediate.

引用

页码：9077 / 9086

页数：10

共 50 条

[41] Rh(II)-Catalysed Condensations of N-Sulfonyl-1,2,3-triazoles with Aminals
Saleh, Nidal
Lacour, Jerome
[J]. SYNOPEN, 2021, 05 (02): : 134 - 137
[42] Highly Regioselective Radical Transformation of N-Sulfonyl-1,2,3-triazoles in Air
Li, Zi
Wei, Qjnghua
Song, Longlong
Han, Wangyujing
Wu, Xiang
Zhao, Yun
Xia, Fei
Liu, Shunying
[J]. ORGANIC LETTERS, 2019, 21 (16) : 6413 - 6417
[43] Rhodium-Catalyzed Tandem Cyclopropanation/Cope Rearrangement of 4-Alkenyl-1-sulfonyl-1,2,3-triazoles with Dienes
Parr, Brendan T.
Davies, Huw M. L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) : 10044 - 10047
[44] Rh(II)-Catalyzed Denitrogenative Reaction of N-Sulfonyl-1,2,3-triazoles with lsatins for the Construction of Indigoids
Pal, Kuntal
Shukla, Rahul K.
Volla, Chandra M. R.
[J]. ORGANIC LETTERS, 2017, 19 (21) : 5764 - 5767
[45] Rh-Catalyzed Denitrogenative Reaction of N-Sulfonyl-1,2,3-triazoles with Isatoic Anhydrides and Oxadiazolones
Pal, Kuntal
Hoque, Abdul
Volla, Chandra M. R.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (11) : 2558 - 2564
[46] Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles to Polysubstituted Pyrroles
Rajasekar, Shanmugam
Anbarasan, Pazhamalai
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 8428 - 8434
[47] Synthesis of Penta-2,4-dien-1-imines and 1,2-Dihydropyridines by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-(Siloxy)furans
Funakoshi, Yuuta
Miura, Tomoya
Murakami, Masahiro
[J]. ORGANIC LETTERS, 2016, 18 (24) : 6284 - 6287
[48] Synthesis of cyclobutane-fused dihydroazepines via rhodium-catalyzed intramolecular [4+3] cycloaddition of 1-sulfonyl-1,2,3-triazoles
Wu, Zhaoqi
Wang, Heng
Chen, Tianci
Xu, Ze-Feng
Li, Chuan-Ying
[J]. TETRAHEDRON LETTERS, 2023, 124
[49] Rhodium-catalyzed synthesis of cyclohexenones via a novel [4+2] annulation
Tanaka, K
Fu, GC
[J]. ORGANIC LETTERS, 2002, 4 (06) : 933 - 935
[50] Synthesis of Enaminones by Rhodium-Catalyzed Denitrogenative Rearrangement of 1-(N-Sulfonyl-1,2,3-triazol-4-yl)alkanols
Miura, Tomoya
Funakoshi, Yuuta
Morimoto, Masao
Biyajima, Tsuneaki
Murakami, Masahiro
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) : 17440 - 17443

← 1 2 3 4 5 →