Facile Synthesis of 2-Alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones

被引：8
作者：
Zeng, Xiao-Hua [1 ,2 ]
Liu, Min [1 ]
Ding, Ming-Wu [1 ]
He, Hong-Wu [1 ]
机构：
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
[2] Yunyang Med Coll, Dept Med Chem, Shiyan, Peoples R China
来源：
SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 10期
基金：
湖北省教育厅重点项目; 中国国家自然科学基金;
关键词：
Aza-Wittig reaction; carbon disulfide; iminophosphorane; isothiocyanate; thieno[2; 3-d]pyrimidin-4(3H)-one; EFFICIENT SYNTHESIS; ANTIMICROBIAL AGENTS; DERIVATIVES; LIGANDS; BONDS;
D O I：
10.1080/00397910903097294
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Isothiocyanate 2, obtained from aza-Wittig reaction of iminophosphorane 1 with CS2, reacted with amine to give 2-thioxo-2,3,5,6,7,8-hexahydrobenzothieno[2,3-d]pyrimidin-4(1H)-ones 4 in the presence of sodium ethoxide. S-Alkylation of 4 produced 2-alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones 5 in good yields.
引用
收藏
页码：1453 / 1460
页数：8
相关论文
共 21 条
[1]  
Briel D, 2003, PHARMAZIE, V58, P836
[2]   Synthesis and preliminary evaluation of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4-ones as antimicrobial agents [J].
Chambhare, RV ;
Khadse, BG ;
Bobde, AS ;
Bahekar, RH .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (01) :89-100
[3]   New efficient synthesis of 2-substituted 5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones [J].
Ding, MW ;
Yang, SJ ;
Zhu, J .
SYNTHESIS-STUTTGART, 2004, (01) :75-79
[4]   Reactions with ethyl-4,5,6,7-tetrahydro-2-isothiocyanato-1-benzothiophene-3-carboxylate. Synthesis of some novel heterocyclic compounds with potential hypnotic activity [J].
Ghorab, MM ;
Heiba, HI ;
ElGawish, MA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 106 (1-4) :85-90
[5]   Synthetic approaches to bridgehead nitrogen methanesulfonamide derivatives of 3-amino-2-thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones, potential COX-2 selective inhibitors [J].
Granata, Giuseppe ;
Barbagallo, Salvatore ;
Perdicaro, Antonio ;
Marrazzo, Agostino ;
Santagati, Andrea ;
Lombardo, Laura ;
Cardile, Venera .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (04) :1099-1104
[6]   Unprecedented replacement of bridging oxygen atoms in polyoxometalates with organic imido ligands [J].
Hao, Jian ;
Xia, Yun ;
Wang, Longsheng ;
Ruhlmann, Laurent ;
Zhu, Yulin ;
Li, Qiang ;
Yin, Panchao ;
Wei, Yongge ;
Guo, Hongyou .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) :2626-2630
[7]   Synthesis and application of some: New thienopyrimidine derivatives as antimicrobial agents [J].
Hozien, ZA ;
Atta, FM ;
Hassan, KM ;
AbdelWahab, AA ;
Ahmed, SA .
SYNTHETIC COMMUNICATIONS, 1996, 26 (20) :3733-3755
[8]   Efficient iminophosphorane-mediated preparation of benzofuro-[3,2-d]pyrimidin-4(3H)-ones and unexpected ring opening products [J].
Hu, Yang-Gen ;
Liu, Ming-Guo ;
Ding, Ming-Wu .
HELVETICA CHIMICA ACTA, 2008, 91 (05) :862-872
[9]   Efficient synthesis and biological evaluation of 1,2,9-trisubstituted 1,9-dihydro-6H-purin-6-ones [J].
Huang, Nian-Yu ;
Liang, Yong-Ju ;
Ding, Ming-Wu ;
Fu, Li-Wu ;
He, Hong-Wu .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (03) :831-833
[10]   Exploration of a new type of antimalarial compounds based on febrifugine [J].
Kikuchi, Haruhisa ;
Yamamoto, Keisuke ;
Horoiwa, Seiko ;
Hirai, Shingo ;
Kasahara, Ryota ;
Hariguchi, Norimitsu ;
Matsumoto, Makoto ;
Oshima, Yoshiteru .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (15) :4698-4706
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