Synthesis of substituted pyrido[3′,2′:4,5] thieno[3,2-c] isoquinolin-5(6H)-ones and their sulfinyl and sulfonyl derivatives

被引：5
作者：
Kalugin, V. E. [1 ]
Shestopalov, A. M. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2017年 / 66卷 / 03期
关键词：
3-cyanopyridine-2(1H)-thiones; methyl 2-(chloromethyl)benzoate; potassium tert-butoxide; domino reactions; pyrido[3',2':4,5]thieno[3,2-c]isoquinolin-5(6H)-ones; pyrido[3',2':4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11-oxides pyrido[3',2':4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11,11-dioxides;
D O I：
10.1007/s11172-017-1766-z
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A method for the synthesis of previously unknown pyrido[3',2':4,5]thieno[3,2-c]isoquinolin-5(6H)-ones was suggested, which includes a condensation reaction of substituted 3-cyanopyridine-2(1H)-thiones with methyl 2-(chloromethyl)benzoate and subsequent treatment of the condensation products with potassium tert-butoxide. The oxidation of the condensation products to sulfoxides or sulfones and subsequent treatment of these compounds with potassium tert-butoxide led to substituted pyrido[3',2':4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11-oxides or substituted pyrido[3',2':4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11,11-dioxides.
引用
收藏
页码：523 / 530
页数：8
相关论文
共 16 条
[1]  
[Anonymous], 2006, DOMINO REACTIONS ORG
[2]   Synthesis of new indeno[1,2-c]isoquinolines:: Cytotoxic non-camptothecin topoisomerase I inhibitors [J].
Cushman, M ;
Jayaraman, M ;
Vroman, JA ;
Fukunaga, AK ;
Fox, BM ;
Kohlhagen, G ;
Strumberg, D ;
Pommier, Y .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (20) :3688-3698
[3]  
GEWALD K, 1974, J PRAKT CHEM, V316, P1030, DOI 10.1002/prac.19743160620
[4]   Synthesis of substituted 5-aminobenzothieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives [J].
Kalugin, V. E. ;
Shestopalov, A. M. .
RUSSIAN CHEMICAL BULLETIN, 2015, 64 (04) :878-882
[5]   Synthesis of substituted benzothieno[3,2-c]isoquinolin-5(6H)-ones and their sulfinyl and sulfonyl derivatives [J].
Kalugin, V. E. ;
Shestopalov, A. M. .
RUSSIAN CHEMICAL BULLETIN, 2014, 63 (11) :2478-2484
[6]   Synthesis of derivatives of pyrido[3′,2′-:4,5]furo[3,2-c]isoquinoline heterocyclic system [J].
Kalugin, V. E. ;
Shestopalov, A. M. .
RUSSIAN CHEMICAL BULLETIN, 2014, 63 (02) :426-430
[7]   A convenient synthesis of benzofuro[3,2-c]isoquinolines and naphtho[1′,2′:4,5]furo[3,2-c]isoquinolines [J].
Kalugin, Victor E. ;
Shestopalov, Anatoly M. .
TETRAHEDRON LETTERS, 2011, 52 (14) :1557-1560
[8]  
KOVTUNENKO VA, 1983, UKR KHIM ZH+, V49, P1099
[9]  
Krauze A.A., 1981, Chem. Heterocycl. Compd, V17, P279, DOI [DOI 10.1007/BF00505994, 10.1007/BF00505994]
[10]  
Prakash J., 2008, CHEM ABSTR, V149, Patent No. 7,393,955
12