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

[1] Synthesis of 5,8-Diamino-Substituted Pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines and Pyrimido[4′,5′:4,5]thieno[2,3-c]isoquinolines
E. G. Paronikyan
Sh. Sh. Dashyan
N. S. Minasyan
G. M. Stepanyan
Russian Journal of Organic Chemistry, 2016, 52 : 576 - 581
[2] Synthesis of Benzo[4,5]furo[3,2-b]thieno[2,3-d]pyridines —Derivatives of a New Heterocyclic System
M. S. Yagodkina-Yakovenko
A. V. Bol’but
M. V. Vovk
Russian Journal of Organic Chemistry, 2018, 54 : 1569 - 1572
[3] Synthesis of Benzo[4,5]furo[3,2-b]thieno[2,3-d]pyridines Derivatives of a New Heterocyclic System
Yagodkina-Yakovenko, M. S.
Bol'but, A. V.
Vovk, M. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 54 (10) : 1569 - 1572
[4] One-pot approach to construct benzo[4,5]thieno[3,2-b]indoles, pyrido [3′,2′:4,5]thieno[3,2-b]indoles and pyrazino[2′,3′:4,5]thieno[3,2-b] indoles based on the Fischer indole synthesis
Irgashev, Roman A.
Steparuk, Alexander S.
Rusinov, Gennady L.
TETRAHEDRON, 2020, 76 (52)
[5] Ring closure reactions of pyrido[2,3-d]pyrimidines to Pyrano[2′,3′:4,5]- and Oxazolo[5′,4′:4,5]pyrido[2,3-d]pyrimidines
Van Tinh, Dang
Stadlbauer, Wolfgang
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (05) : 1359 - 1364
[6] SYNTHETIC INVESTIGATION ON ISOTHIAZOLO-[5,4-B]-PYRIDINES AND ISOTHIAZOLO-[4,5-C]-PYRIDINES
CHIMICHI, S
NESI, R
PONTICELLI, F
TEDESCHI, P
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05): : 1477 - 1480
[7] Synthesis and properties of substituted isoxazolo[3′,4′:4,5]thieno[2,3-b]pyridines
Vasilin, VK
Kaigorodova, EA
Firgang, SI
Krapivin, GD
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (03): : 462 - 472
[8] Synthesis and properties of substituted isoxazolo[3′,4′:4,5]- thieno[2,3-b]pyridines
Vasilin V.K.
Kaigorodova E.A.
Firgang S.I.
Krapivin G.D.
Chemistry of Heterocyclic Compounds, 2004, 40 (3) : 377 - 386
[9] Synthesis and anticonvulsant activity of isothiazolo[5,4-b]pyrano(thiopyrano)[4,3-d]pyridine and isothiazolo[4,5-b]-2,7-naphthyridine derivatives
Paronikyan E.G.
Noravyan A.S.
Dzhagatspanyan I.A.
Nazaryan I.M.
Paronikyan R.G.
Pharmaceutical Chemistry Journal, 2002, 36 (9) : 465 - 467
[10] Synthesis and anticonvulsant activity of pyrano[4′,3′:4,5]pyrido[2,3-b]furo[3,2-d]pyrimidine and pyrano[4′,3′:4,5]pyrido[2,3-b]furo[3,2-d]pyridine derivatives
Paronikyan E.G.
Oganisyan A.Kh.
Noravyan A.S.
Paronikyan R.G.
Dzhagatspanyan I.A.
Pharmaceutical Chemistry Journal, 2002, 36 (8) : 413 - 414

← 1 2 3 4 5 →