Synthesis of Functionalized 2,3-Dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-one via Intramolecular Electrophilic Cyclization

被引：2
|
作者：
Kut, N. M. [1 ]
Onysko, M. Yu. [1 ]
Lendel, V. G. [1 ]
机构：
[1] Uzhgorod Natl Univ, UA-88000 Uzhgorod, Ukraine
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 56卷 / 07期
关键词：
electrophilic cyclization; halogen-containing electrophile; p-methoxyphenyltellurium trichloride; regioselectivity; 3-(2-methylprop-2-en-1-yl)-2-sulfanylidene-7-(trifluoromethyl)-2; 3-dihydroquinazolin-4(1H)-one; 2; 3-dihydro-5H-[1; 3]thiazolo[2; 3-b]quinazolin-5-one; STEREOSELECTIVE-SYNTHESIS; ANTICANCER ACTIVITY; DERIVATIVES; SELENIUM; SYSTEMS; HETEROCYCLIZATION; ANTIBACTERIAL; INHIBITORS; DRUGS;
D O I：
10.1134/S1070428020070088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
3-(2-Methylprop-2-en-1-yl)-2-sulfanylidene-7-(trifluoromethyl)-2,3-dihydroquinazolin-4(1H)-one reacted with halogens (bromine and iodine), chalcogen tetrahalides, andp-methoxyphenyltellurium trichloride in a regioselective manner to give linearly fused 2-halomethyl-2-methyl-5-oxo-8-(trifluoromethyl)-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolinium trihalides, 2-methyl-5-oxo-2-[(trihalo-lambda(4)-chalcogenyl)methyl]-8-(trifluoromethyl)-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolinium halides, and 2-{[dichloro(4-methoxyphenyl)-lambda(4)-tellanyl]methyl}-8-(trifluoromethyl)-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-one, respectively.
引用
收藏
页码：1174 / 1180
页数：7
相关论文
共 50 条
  • [21] Synthesis of Some New Thieno[2,3-b]pyridines, Pyrimidino[4′,5′:4,5]thieno[2,3-b]pyridine and Pyridines Incorporating 5-Bromobenzofuran-2-yl Moiety
    Abdelriheem, Nadia Abdelhamed
    Ahmad, Sayed Abdel-Kader
    Abdelhamid, Abdou Osman
    MOLECULES, 2015, 20 (01) : 822 - 838
  • [22] A General Method for the Synthesis of 5H-Benzo[b]-, Carbazolo[2,3-b]- and Indolo[2,3-b]carbazole Derivatives via Copper(II) Triflate-Catalyzed Heteroannulation
    Prakash, K. S.
    Nagarajan, Rajagopal
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (08) : 1566 - 1578
  • [23] Facile synthesis of thiochromeno[2,3-b]indol-11(6H)-ones and pyrido[3′,2′:5,6]thiopyrano[2,3-b]indol-5(10H)-ones
    Kiamehr, Mostafa
    Moghaddam, Firouz Matloubi
    Semeniuchenko, Volodymyr
    Villinger, Alexander
    Langer, Peter
    Iaroshenko, Viktor O.
    TETRAHEDRON LETTERS, 2013, 54 (37) : 5018 - 5021
  • [24] A concise construction of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones via an unusual TBHP/Na2CO3 promoted cascade oxidative cyclization and interrupted Dimroth rearrangement
    Zhou, Zhi-Wen
    Jia, Feng-Cheng
    Xu, Cheng
    Jiang, Shi-Fen
    Wu, Yan-Dong
    Wu, An-Xin
    CHEMICAL COMMUNICATIONS, 2017, 53 (06) : 1056 - 1059
  • [25] Microwave assisted synthesis of 2,3-dihydro-4H-benzo[4,5]thiazolo[3,2-a]furo[2,3-d]pyrimidin-4-ones and 6,7-dihydro-5H-furo[2,3-d]thiazolo [3,2-a]pyrimidin-5-ones using Mn(OAc)3
    Ustalar, Ash
    Yilmaz, Mehmet
    TETRAHEDRON LETTERS, 2017, 58 (06) : 516 - 519
  • [26] A Straightforward Approach to Substituted 2-(Hydroxymethyl)-2,3-dihydrofuro[2,3-b] pyridines and 3-Hydroxy-3,4-dihydro-2H-pyrano[ 2,3-b] pyridines
    Hajbi, Youssef
    Suzenet, Franck
    Khouili, Mostafa
    Lazar, Said
    Guillaumet, Gerald
    SYNTHESIS-STUTTGART, 2010, (08): : 1349 - 1355
  • [27] Synthesis of 2-(1-aryl-1H-tetrazol-5-yl)-thieno[2,3-b]pyridine derivatives
    Koltsov, Nikolai Yu
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (08) : 768 - 772
  • [28] Synthesis of 2-(1-aryl-1H-tetrazol-5-yl)-thieno[2,3-b]pyridine derivatives
    Nikolai Yu. Koltsov
    Chemistry of Heterocyclic Compounds, 2019, 55 : 768 - 772
  • [29] One-pot and solvent-free synthesis of 3-(9-hydroxy-3-methoxy-7-aryl-6,7,9,10-tetrahydro-5H-benzo [h]thiazolo [2,3-b] quinazolin-9-yl)-2H-chromen-2-ones and their antibacterial evaluation
    Velpula, Ravibabu
    Banothu, Janardhan
    Gali, Rajitha
    Sargam, Yakaiah
    Bavantula, Rajitha
    TURKISH JOURNAL OF CHEMISTRY, 2015, 39 (03) : 620 - 629
  • [30] A convenient one-pot synthesis of novel functionalized thiophene, thieno[2,3-b] thiophene, thiopyran, and thiopyrano[2,3-b]thiopyran bearing phosphonate groups
    Ali, Tarik E.
    Assiri, Mohammed A.
    JOURNAL OF SULFUR CHEMISTRY, 2021, 42 (05) : 490 - 498
12345