Synthesis of Thiochromans via [3+3] Annulation of Aminocyclopropanes with Thiophenols

被引：9

作者：

Wang, Ming-Ming ^{[1
]}

Jeon, Seongmin ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, Inst Sci & Ingn Chim, CH-1015 Lausanne, Switzerland

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 22期

基金：

瑞士国家科学基金会;

关键词：

D O I：

10.1021/acs.orglett.0c03528

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the one-pot synthesis of 4-amino thiochromans using simple aminocyclopropanes and thiophenols through a formal [3+3] annulation reaction. This reaction proceeds under mild conditions with good functional group tolerance. The thiochroman core was formed with complete regioselectivity, and modification of complex drug molecules containing an aminocyclopropane was also realized.

引用

页码：9123 / 9127

页数：5

共 50 条

[41] DMAP-Catalyzed [3+3] Annulation of Cyclopropenones with α-Bromoketones for Synthesis of 2-Pyrones
Qiao, Lijuan
He, Xin
Yang, Lulu
Babu, Kaki Raveendra
Wu, Yong
Tang, Yuhai
Xu, Silong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (15)
[42] Enantioselective Synthesis of Spirocyclohexadienones by NHC-Catalyzed Formal [3+3] Annulation Reaction of Enals
Yetra, Santhivardhana Reddy
Mondal, Santigopal
Mukherjee, Subrata
Gonnade, Rajesh G.
Biju, Akkattu T.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (01) : 268 - 272
[43] [3+3] Annulation of donor-acceptor cyclopropanes with mercaptoacetaldehyde: application to the synthesis of tetrasubstituted thiophenes
Sathishkannan, Gopal
Srinivasan, Kannupal
CHEMICAL COMMUNICATIONS, 2014, 50 (31) : 4062 - 4064
[44] Organocatalyzed enantioselective [3+3] annulation for the direct synthesis of conformationally constrained cyclic tryptophan derivatives
Wu, L. -L.
Zheng, Y.
Wang, Y. -M.
Zhou, Z. -H.
RSC ADVANCES, 2016, 6 (14): : 11602 - 11608
[45] DIASTEREOSELECTIVE SYNTHESIS OF ACTINOBOLIN FROM D-GLUCOSE BY APPLICATION OF A NOVEL [3+3]-ANNULATION
WARD, DE
KALLER, BF
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15): : 4230 - 4238
[46] (3+3)-Annulation of Donor-Acceptor Cyclopropanes with Diaziridines
Chagarovskiy, Alexey O.
Vasin, Vladimir S.
Kuznetsov, Vladimir V.
Ivanova, Olga A.
Rybakov, Victor B.
Shumsky, Alexey N.
Makhova, Nina N.
Trushkov, Igor V.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) : 10338 - 10342
[47] Enantioselective Synthesis of Tropanes via [3+3] Annulation of Cyclic Azomethine Ylides with Substituted 2-Vinylindoles and 2-Vinylpyrroles
Zheng, Xing
Yang, Wu-Lin
Liu, Yang-Zi
Wu, Shu-Xiao
Deng, Wei-Ping
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (15) : 2843 - 2853
[48] An Approach for the Synthesis of Pyrazolo[1,5-a]pyrimidines via Cu(II)-Catalyzed [3+3] Annulation of Saturated Ketones with Aminopyrazoles
Ren, Jian
Ding, Shihua
Li, Xiaonian
Bi, Ran
Zhao, Qinshi
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (18): : 12762 - 12771
[49] Synthesis of novel hexahydroquinolines and 6-amino-2-oxopyridine-3,5-dicarbonitriles incorporating sulfamethoxazole via [3+3] annulation
Abdelmoniem, Amr M.
Abdelrahman, Mohamed Gamal Mohamed
Ghozlan, Said Ahmed Soliman
Abdelhamid, Ismail A.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (12) : 3387 - 3395
[50] Catalyst-Controlled Divergent Synthesis of 2H-Chromenes via [3+3] Annulation of Vinyl Sulfoxonium Ylides with Quinones
Deshwal, Shalu
Davas, Daksh Singh
Bhardwaj, Srashti
Vaitla, Janakiram
ORGANIC LETTERS, 2024, 26 (04) : 809 - 813

← 1 2 3 4 5 →