Synthesis of Isomeric Isothiazolo[4′,3′:4,5]- and Isothiazolo[4′,5′:4,5]thieno[3,2-b]pyrano[2,3-d]pyridines by Combination of Domino Reactions

被引：9

作者：

Shestopalov, Anatoliy M. ^{[1
]}

Larionova, Natalia A. ^{[1
]}

Fedorov, Alexander E. ^{[1
]}

Rodinovskaya, Lyudmila A. ^{[1
]}

Mortikov, Valery Yu. ^{[1
]}

Zubarev, Andrey A. ^{[1
]}

Bushmarinov, Ivan S. ^{[2
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

ACS COMBINATORIAL SCIENCE | 2013年 / 15卷 / 10期

关键词：

disodium; 4-cyanoisothiazole-3; 5-dithiolate; ethyl; 4-chloroacetoacetate; isothiazoles; isothiazolothienopyranopyridines; domino reaction; regioselectivity; BIOLOGICAL EVALUATION; MULTICOMPONENT SYNTHESIS; DERIVATIVES; 4-HYDROXYCOUMARIN; ISOTHIAZOLES;

D O I：

10.1021/co400066y

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Isothiazolothienopyridines have been prepared by a domino reaction (the S(N)2 reaction -> the Thorpe-Ziegler reaction -> the Thorpe-Guareschi reaction type) from disodium 4-cyanoisothiazole-3,5-dithiolate. By changing the order of addition of the alkylation reagents in the reaction with disodium 4-cyanoisothiazole-3,5-dithiolate both possible isomers of the isothiazolothienopyridines are synthesized. These isomers were further used in three-component domino reaction (the Knoevenagel reaction -> the Michael reaction -> the hetero-Thorpe-Ziegler reaction type) to obtain wide range of isomeric isothiazolothienopyranopyridines.

引用

页码：541 / 545

页数：5

共 50 条

[21] Synthesis, Characterization, and Field-Effect Transistor Performance of Thieno[3,2-b]thieno[2′,3′:4,5]thieno [2,3-d]thiophene Derivatives
Liu, Ying
Wang, Ying
Wu, Weiping
Liu, Yunqi
Xi, Hongxia
Wang, Limin
Qiu, Wenfieng
Lu, Kun
Du, Chunyon
Yu, Gui
ADVANCED FUNCTIONAL MATERIALS, 2009, 19 (05) : 772 - 778
[22] Synthesis and anticonvulsive activity of a series of new pyrano(thiopyrano,pyrido)-[4′,3′:4,5]thieno[2,3-d]pyrimidines
Mkrtchyan A.P.
Kazaryan S.G.
Noravyan A.S.
Dzhagatspanyan I.A.
Nazaryan I.M.
Akopyan A.G.
Pharmaceutical Chemistry Journal, 1998, 32 (9) : 469 - 473
[23] Synthesis and anticonvulsant activity of pyrano[4′,3′:4,5] pyrido[2,3-b]thieno[3,2-d] pyrimidine derivatives and pyrimido[5′, 4′:2,3]-thieno[2,3-c]isoquinoline derivatives
Paronikyan E.G.
Noravyan A.S.
Akopyan Sh.F.
Dzhagatspanyan I.A.
Nazaryan I.M.
Paronikyan R.G.
Pharmaceutical Chemistry Journal, 2007, 41 (9) : 466 - 469
[24] Synthesis of new heteroaromatic nitrogen ligands:: Pyrimido-[4",5":4′,5′]-thieno[3′,2′:4,5]thieno[3,2-d]pyrimidines and 1,2,3-triazine[4",5":4′,5′]thieno[3′,2′:4,5]thieno[3,2-d]-1,2,3-triazines
Blanco, Gerardo
Quintela, Jose M.
Peinador, Carlos
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (04) : 1051 - 1056
[25] Organic sensitizers featuring 9H-thieno [2′,3′:4,5]thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]pyrrole core for high performance dye-sensitized solar cells
Wang, Zhihui
Miu, Lihai
Yao, Huiyun
Liang, Mao
Yan, Suhao
Wang, Jiawei
Guo, Tao
Zhang, Lijing
Chen, Jing
Xue, Song
DYES AND PIGMENTS, 2019, 162 : 126 - 135
[26] Synthesis of Derivatives of Cyclopenta[4',5']Pyrido-[3',2':4,5]Thieno[3,2-d]Pyrimidines and Pyrimido[5',4':2,3]-Thieno[2,3-c]Isoquinolines
E. G. Paronikyan
Sh. Sh. Dashyan
A. S. Noravyan
N. S. Minasyan
Chemistry of Heterocyclic Compounds, 2014, 50 : 1188 - 1194
[27] Synthesis of Derivatives of Cyclopenta[4',5']Pyrido-[3',2':4,5]Thieno[3,2-d]Pyrimidines and Pyrimido[5',4':2,3]-Thieno[2,3-c]Isoquinolines
Paronikyan, E. G.
Dashyan, Sh. Sh.
Noravyan, A. S.
Minasyan, N. S.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (08) : 1188 - 1194
[28] Synthesis of pyrido[2′,3′:4,5]thieno[2,3-d]pyrimidines through Friedlander reactions
Abdel-Mohsen, Shawkat A.
Geies, Ahmed A.
JOURNAL OF CHEMICAL RESEARCH, 2007, (12) : 689 - 692
[29] Synthesis and reactions of naphtho[1′,2′:4,5]furo[3,2-b]pyridine and naphtho[1′,2′:4,5]furo[3,2-d]pyrimidine derivatives
Badr, M. Z. A.
Kamal-El-Dean, A. M.
Moustafa, O. S.
Zaki, R. M.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2007, 54 (04) : 1045 - 1052
[30] Synthesis of a novel tetracyclic pyrido[3',2':4,5]thieno[3,2-b]indole system
E. A. Kanishcheva
V. K. Vasilin
D. R. Kasimova
T. A. Stroganova
G. D. Krapivin
Chemistry of Heterocyclic Compounds, 2013, 48 : 1883 - 1885

← 1 2 3 4 5 →