Base catalyzed reaction of 1,4-dithiane-2,5-diol with α-oxoketene dithioacetals: a new general method for the synthesis of 2-methylthio-3-aroyl/heteroaroyl thiophenes

被引：20

作者：

Kumara, C. S. Pradeepa ^{[1
,2
]}

Gowda, G. Byre ^{[1
,2
]}

Kumar, K. S. Vinay ^{[1
]}

Ramesh, N. ^{[2
]}

Sadashiva, M. P. ^{[1
]}

Junjappa, H. ^{[2
]}

机构：

[1] Univ Mysore, Dept Studies Chem, Mysore 570006, Karnataka, India

[2] REVA Inst Sci & Management, Dept Chem, Bengaluru 560064, India

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 38期

关键词：

alpha-Oxoketenedithio acetals; 1,4-Dithiane-2,5-diol; Mercapto acetaldehyde; DERIVATIVES;

D O I：

10.1016/j.tetlet.2016.08.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alpha-oxoketene dithioacetals and 1,4-dithiane-2,5-diol a dimer of mercapto acetaldehyde, react in the presence of anhydrous potassium carbonate in boiling ethanol to yield the corresponding 2-(methylthio)-3-aroyl/heteroaroyl thiophenes in 55-70% overall yields. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：4302 / 4305

页数：4

共 26 条

[1] Domino Synthesis of Tetrasubstituted Thiophenes from 1,3-Enynes with Mercaptoacetaldehyde [J].

Bharathiraja, Ganesan ;

Sathishkannan, Gopal ;

Punniyamurthy, Tharmalingam .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06) :2670-2674

[2] Biotransformation reactions of five-membered aromatic heterocyclic rings [J].

Dalvie, DK ;

Kalgutkar, AS ;

Khojasteh-Bakht, SC ;

Obach, RS ;

O'Donnell, JP .

CHEMICAL RESEARCH IN TOXICOLOGY, 2002, 15 (03) :269-299

[3] SYNTHESIS OF ALPHA-PYRONES FROM ALPHA-OXO KETENE DITHIOACETALS [J].

DIETER, RK ;

FISHPAUGH, JR .

TETRAHEDRON LETTERS, 1986, 27 (33) :3823-3826

[4] Base catalyzed reaction of ethyl thioglycolate with β-aryl-β-(methylthio) acroleins: a general method for the synthesis of 2-carbethoxy-5-substituted/4,5-annulated thiophenes in high overall yields [J].

Gowda, G. Byre ;

Kumara, C. S. Pradeepa ;

Ramesh, N. ;

Sadashiva, M. P. ;

Junjappa, H. .

TETRAHEDRON LETTERS, 2016, 57 (08) :928-931

[5] A short, practical synthesis of 3-thiophenecarboxaldehyde [J].

Huckabee, BK ;

Stuk, TL .

SYNTHETIC COMMUNICATIONS, 2001, 31 (10) :1527-1530

[6] ALPHA-OXOKETENE-S,S-ACETAL, N,S-ACETAL AND N,N-ACETAL - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].

JUNJAPPA, H ;

ILA, H ;

ASOKAN, CV .

TETRAHEDRON, 1990, 46 (16) :5423-5506

[7] Synthesis of Thiophene-Based TAK-779 Analogues by C-H Arylation [J].

Junker, Anna ;

Yamaguchi, Junichiro ;

Itami, Kenichiro ;

Wuensch, Bernhard .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11) :5579-5586

[8] Synthesis and antioxidant activity of 1,3,4-oxadiazole tagged thieno[2,3-d] pyrimidine derivatives [J].

Kotaiah, Y. ;

Harikrishna, N. ;

Nagaraju, K. ;

Rao, C. Venkata .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 58 :340-345

[9] An efficient synthesis of N-substituted 3-nitrothiophen-2-amines [J].

Kumar, Sundaravel Vivek ;

Muthusubramanian, Shanmugam ;

Carlos Menendez, J. ;

Perumal, Subbu .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 :1707-1712

[10] A new general method for the synthesis of thiophenes through acid mediated cyclization of mixed acetals derived from β-oxodithiates and bromoacetaldehyde acetal [J].

Kumara, C. S. Pradeepa ;

Gowda, G. Byre ;

Ramesh, N. ;

Sadashiva, M. P. ;

Junjappa, H. .

TETRAHEDRON LETTERS, 2016, 57 (23) :2520-2523

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