The synthesis of substituted 5-aminopyrido[3',2':4,5]thieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives

被引：3

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 | 2018年 / 67卷 / 05期

关键词：

3-cyanopyridine-2(1H)-thiones; 2-(chloromethyl)benzonitrile; potassium tert-butoxide; domino reactions; 5-aminopyrido[3 ',2 ':4,5]thieno[3,2-c]isoquinolines; sulfoxides; sulfones; heterocyclization; INHIBITORS; PYRIDINES;

D O I：

10.1007/s11172-018-2155-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

5-Aminopyrido[3',2':4,5]thieno[3,2-c]isoquinolines were synthesized via alkylation of 3-cyanopyridine-2(1H)-thiones with 2-(chloromethyl)benzonitrile followed by treatment of the products with potassium tert-butoxide. The oxidation of the alkylated products to corresponding sulfoxides or sulfones followed by treatment with potassium tert-butoxide provided the corresponding 11-oxides or 11,11-dioxides.

引用

页码：902 / 911

页数：10

共 16 条

[1] Synthesis of new indeno[1,2-c]isoquinolines:: Cytotoxic non-camptothecin topoisomerase I inhibitors
Cushman, M
Jayaraman, M
Vroman, JA
Fukunaga, AK
Fox, BM
Kohlhagen, G
Strumberg, D
Pommier, Y
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (20) : 3688 - 3698
[2] GEWALD K, 1974, J PRAKT CHEM, V316, P1030, DOI 10.1002/prac.19743160620
[3] Synthesis of substituted pyrido[3′,2′:4,5] thieno[3,2-c] isoquinolin-5(6H)-ones and their sulfinyl and sulfonyl derivatives
Kalugin, V. E.
Shestopalov, A. M.
[J]. RUSSIAN CHEMICAL BULLETIN, 2017, 66 (03) : 523 - 530
[4] Synthesis of substituted 5-aminobenzothieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives
Kalugin, V. E.
Shestopalov, A. M.
[J]. 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
Kalugin, V. E.
Shestopalov, A. M.
[J]. 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
Kalugin, V. E.
Shestopalov, A. M.
[J]. 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
Kalugin, Victor E.
Shestopalov, Anatoly M.
[J]. TETRAHEDRON LETTERS, 2011, 52 (14) : 1557 - 1560
[8] Krauze A.A., 1981, Chem. Heterocycl. Compd, V17, P279, DOI [DOI 10.1007/BF00505994, 10.1007/BF00505994]
[9] CONDENSED PYRIDINES .3. ARYLIDENETHIO(SELENO)ACETAMIDES IN THE SYNTHESIS OF "4-ARYL-3-CYANO-2[1H]PYRIDINETHIONES AND 4-ARYL-3-CYANO-2[1H]PYRIDINESELENONES
LITVINOV, VP
PROMONENKOV, VK
SHARANIN, YA
SHESTOPALOV, AM
RODINOVSKAYA, LA
MORTIKOV, VY
BOGDANOV, VS
[J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1985, 34 (09): : 1940 - 1947
[10] A KINETIC STUDY OF THE REACTION OF SUBSTITUTED BENZYL CHLORIDES WITH TERTIARY AMINES
MUKAIYAMA, T
TANAKA, H
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1956, 29 (08) : 908 - 913

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