Domino Synthesis of Thiochromenes through Cu-Catalyzed Incorporation of Sulfur Using Xanthate Surrogate

被引：30

作者：

Muthupandi, Pandi ^{[1
]}

Sundaravelu, Nallappan ^{[1
]}

Sekar, Govindasamy ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 04期

关键词：

MICHAEL-ALDOL REACTIONS; ONE-POT SYNTHESIS; BOND FORMATION; RECEPTOR; ANALOGS; BENZOTHIAZOLES; SELECTIVITY; CYCLIZATION; INHIBITORS;

D O I：

10.1021/acs.joc.6b02740

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient domino reaction has been developed for the synthesis of thiochromenes through Cu-catalyzed in situ incorporation of sulfur. This domino method avoids the use of less accessible and unpleasant arenethiols as starting materials, instead utilizes very stable aryl halides along with potassium ethyl xanthate as an odorless sulfur surrogate. The domino methodology proceeds through C-(aryl)-S coupling, thioester cleavage, sulfa-Michael addition, aldol reaction, and elimination reaction sequences to provide thiochromenes in good yields

引用

页码：1936 / 1942

页数：7

共 50 条

[41] Convenient synthesis of ferrocene amines via Cu-catalyzed coupling reaction
Wu, Jinsheng
Li, Xiaolong
Yang, Mingyu
Gao, Yujie
Lv, Qianru
Chen, Baohua
CANADIAN JOURNAL OF CHEMISTRY, 2008, 86 (09) : 871 - 874
[42] Enantio- and diastereoselective synthesis of 1,2-hydroxyboronates through Cu-Catalyzed additions of alkylboronates to aldehydes
20152200892720
Meek, Simon J., 1600, American Chemical Society (137):
[43] Total Synthesis of (R, R, R)-α-Tocopherol Through Asymmetric Cu-Catalyzed 1,4-Addition
Termath, Andreas Ole
Sebode, Hanna
Schlundt, Waldemar
Stemmler, Rene T.
Netscher, Thomas
Bonrath, Werner
Schmalz, Hans-Guenther
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (38) : 12051 - 12055
[44] Synthesis of Pyrrolo[2,1-a]isoquinolines through Cu-Catalyzed Condensation/Addition/Oxidation/Cyclization Cascade
Cui, Hai-Lei
Chen, Xiao-Hui
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (22): : 15435 - 15447
[45] Total Synthesis of (R, R, R)-γ-Tocopherol through Cu-Catalyzed Asymmetric 1,2-Addition
Wu, Zhongtao
Harutyunyan, Syuzanna R.
Minnaard, Adriaan J.
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (44) : 14250 - 14255
[46] Enantio- and Diastereoselective Synthesis of 1,2-Hydroxyboronates through Cu-Catalyzed Additions of Alkylboronates to Aldehydes
Joannou, Matthew V.
Moyer, Brandon S.
Meek, Simon J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (19) : 6176 - 6179
[47] Convenient Synthesis of Arylboronates through a Synergistic Pd/Cu-Catalyzed Miyaura Borylation Reaction under Atmospheric Conditions
Ratniyom, Jadsada
Dechnarong, Nattanee
Yotphan, Sirilata
Kiatisevi, Supavadee
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (07) : 1381 - 1385
[48] Fe-Cu catalyzed synthesis of symmetrical and unsymmetrical diaryl thioethers using 1,3-benzoxazole-2-thiol as a sulfur surrogate
Tber, Z.
Hiebel, M. -A.
El Hakmaoui, A.
Akssira, M.
Guillaumet, G.
Berteina-Raboin, S.
RSC ADVANCES, 2016, 6 (76): : 72030 - 72036
[49] Cu-Catalyzed Expeditious Synthesis of N-Benzylaminoheter-ocycles Using N-Tosylhydrazones and Aminoheteroarenes
Pilania, Meenakshi
Velladurai, Arun
Tantak, Mukund P.
Kumar, Dalip
CHEMISTRYSELECT, 2016, 1 (20): : 6368 - 6373
[50] Novel Cu-catalyzed methods for the synthesis of fused thiazoles using S,N-diarylation reaction
Beresneva, T.
Popelis, J.
Abele, E.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (02) : 345 - 347

← 1 2 3 4 5 →