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

[41] Multicomponent Synthesis of Novel Functionalized Pyrano[2',3':4,5]pyrimido[1,6-b][1,2,4,5]triazaphosphinines
Ali, T. E.
Bakhotmah, D. A.
Assiri, M. A.
Yahia, I. S.
Zahran, H. Y.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (03) : 469 - 475
[42] Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group
Hosny, Mona A.
Zaki, Yasser H.
Mokbel, Wafaa A.
Abdelhamid, Abdou O.
BMC CHEMISTRY, 2019, 13 (1)
[43] Microwave assisted synthesis of 2,3-dihydro-4H-benzo[4,5]thiazolo [3,2-a]furo[2,3-d] pyrimidin-4-ones by radical addition of 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a] pyrimidin-4-ones to various conjugated alkenes and dienes mediated Mn(OAc)3
Yilmaz, Mehmet
Inal, Asl i Ustalar
TETRAHEDRON, 2022, 116
[44] A New Entry to Benzo[4,5]furo[3,2-b]pyridines via N-(Benzofuran-3-yl)iminophosphorane
Funicello, Maria
Laboragine, Valeria
Pandolfo, Rocco
Spagnolo, Piero
SYNLETT, 2010, (01) : 77 - 80
[45] Synthesis of thiopyrano[4",3":4′,5′]pyrido[3′,2′:4, 5]furo[3,2-d]pyrimidines
Ahmed, Essam Kh.
Ameen, Mohamed A.
CHINESE CHEMICAL LETTERS, 2010, 21 (06) : 669 - 673
[46] Regioselective synthesis of new 5-methyl-5H-pyrimido[4′,5′:4,5][1,3]thiazino [3,2-a]perimidines
Firoozi, Neda
Bakavoli, Mehdi
Eshghi, Hossein
Ramezanian, Navid
JOURNAL OF SULFUR CHEMISTRY, 2017, 38 (05) : 488 - 495
[47] Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
Do, Hoang Huy
Ullah, Saif
Villinger, Alexander
Lecka, Joanna
Sevigny, Jean
Ehlers, Peter
Iqbal, Jamshed
Langer, Peter
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 2830 - 2839
[48] 1,3-Bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione
Yin, Xuelian
Kim, Sung Min
Song, Yang-Heon
MOLBANK, 2022, 2022 (03)
[49] Synthesis and anti-mitotic activity of 6,7-dihydro-4H-isothiazolo [4,5-b]pyridin-5-ones: In vivo and cell-based studies
Semenov, Victor V.
Lichitsky, Boris V.
Komogortsev, Andrey N.
Dudinov, Arkady A.
Krayushkin, Mikhail M.
Konyushkin, Leonid D.
Atamanenko, Olga P.
Karmanova, Irina B.
Strelenko, Yuri A.
Shor, Boris
Semenova, Marina N.
Kiselyov, Alex S.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 125 : 573 - 585
[50] Synthesis and DNase I inhibitory properties of some 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines
Mavrova, Anelia Ts.
Dimov, Stefan
Yancheva, Denitsa
Kolarevic, Ana
Ilic, Budimir S.
Kocic, Gordana
Smelcerovic, Andrija
BIOORGANIC CHEMISTRY, 2018, 80 : 693 - 705

← 1 2 3 4 5 →