Expeditious Synthesis of Isoquinolone Derivatives by Rhodium(I)-Catalyzed Annulation Reaction through C-C Bond Cleavage

被引：24

作者：

He, Yiyi ^{[1
]}

Yuan, Chengsha ^{[1
]}

Jiang, Zeqi ^{[1
]}

Shuai, Li ^{[1
]}

Xiao, Qing ^{[1
]}

机构：

[1] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 01期

关键词：

CATALYZED OXIDATIVE COUPLING/CYCLIZATION; DENITROGENATIVE ALKYNE INSERTION; ACTIVATION TOTAL-SYNTHESIS; H/N-H ACTIVATION; BIOLOGICAL EVALUATION; O BOND; REGIOSELECTIVE SYNTHESIS; SITE-SELECTIVITY; INTERNAL OXIDANT; NITRENE TRANSFER;

D O I：

10.1021/acs.orglett.8b03653

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(I)-catalyzed intermolecular cyclization between isocyanates and benzocyclobutenols leading to isoquinolin-1(2H)-ones through selective cleavage of a C-C bond has been realized. Exploiting the same strategy, we developed a Rh(I)-catalyzed three-component reaction of benzocyclobutenols, isonitriles, and sulfonyl azides to access isoquinolin-1(2H)-imines. These procedures provide unique and expeditious access to isoquinolone derivatives which are otherwise difficult to prepare in satisfactory yields with excellent functional-group tolerance under mild reaction conditions.

引用

页码：185 / 189

页数：5

共 50 条

[31] Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
Chen, Wei-Li
Wu, Si-Yi
Mo, Xue-Ling
Wei, Liu-Xu
Liang, Cui
Mo, Dong-Liang
ORGANIC LETTERS, 2018, 20 (12) : 3527 - 3530
[32] Rhodium-catalyzed activation and functionalization of the C-C bond of biphenylene
Iverson, CN
Jones, WD
ORGANOMETALLICS, 2001, 20 (26) : 5745 - 5750
[33] Enantioselective Rhodium-catalyzed C-C Bond Activation of Cyclobutanones
Souillart, Laetitia
Cramer, Nicolai
CHIMIA, 2015, 69 (04) : 187 - 190
[34] Direct oxidative arylation via rhodium-catalyzed C-C bond cleavage of secondary alcohols with arylsilanes
Chen, Kang
Li, Hu
Li, Yang
Zhang, Xi-Sha
Lei, Zhi-Quan
Shi, Zhang-Jie
CHEMICAL SCIENCE, 2012, 3 (05) : 1645 - 1649
[35] Rhodium-Catalyzed C-C Bond Cleavage: Construction of Acyclic Methyl Substituted Quaternary Stereogenic Centers
Seiser, Tobias
Cramer, Nicolai
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) : 5340 - +
[36] Copper-Catalyzed Synthesis of α-Thioaryl Carbonyl Compounds Through S-S and C-C Bond Cleavage
Zou, Liang-Hua
Priebbenow, Daniel L.
Wang, Long
Mottweiler, Jakob
Bolm, Carsten
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) : 2558 - 2563
[37] Catalytic selective cleavage of a strong C-C single bond by rhodium in solution
Liou, SY
van der Boom, ME
Milstein, D
CHEMICAL COMMUNICATIONS, 1998, (06) : 687 - 688
[38] Iron-Catalyzed C-C Bond Cleavage and C-N Bond Formation
Li, Wenjuan
Zheng, Xiaojian
Li, Zhiping
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 181 - 190
[39] A novel chlorotris(triphenylphosphine)rhodium(I) mediated intramolecular C-C bond forming reaction
Biju, PJ
Rao, GSRS
CHEMICAL COMMUNICATIONS, 1999, (21) : 2225 - 2226
[40] Iron-catalyzed azidation of cyclobutanol by C-C bond cleavage
Liu, Xiaoyuan
Wang, Limei
Zhan, Jincheng
Sun, Shutao
Liu, Lei
Li, Wei
Wan, Qian
TETRAHEDRON LETTERS, 2024, 140

← 1 2 3 4 5 →