Pd-Catalyzed Regioselective Tandem C-S/C-N Bond Formation for Modular Synthesis of Pyrimidine-Fused Benzothiazoles from o -Dihaloarenes and 3,4-Dihydropyrimidin-2-thiones

A Pd-catalyzed annulation reaction for the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives via regioselective tandem C-S/C-N bond formation was developed. With PdCl2(PPh3)(2) as the precatalyst, Davephos as the ligand, and K2CO3 as the base, the reactions of various 3,4-dihydropyrimidin-2-t...

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Published inSynthesis (Stuttgart) Vol. 56; no. 13; pp. 2005 - 2014
Main Authors Hu, Xuying, Liu, Ruiqi, Fu, Shiwen, Shi, Lianxu, Chen, Chunxia, Peng, Jinsong
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 02.07.2024
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
palladium catalysis
annulation
C-N bond formation
HETEROCYCLES
ALPHA-CARBOLINES
C-S bond formation
pyrimidobenzothiazoles
CASCADE
o -dihaloarenes
ARYL AMINATION
CYCLIZATION
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Summary:A Pd-catalyzed annulation reaction for the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives via regioselective tandem C-S/C-N bond formation was developed. With PdCl2(PPh3)(2) as the precatalyst, Davephos as the ligand, and K2CO3 as the base, the reactions of various 3,4-dihydropyrimidin-2-thiones with o-dihaloarenes proceeded smoothly, and the desired products were obtained in moderate to good yields.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-2311-3930