Synthesis 2024; 56(13): 2005-2014
DOI: 10.1055/a-2311-3930
paper

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

Xuying Hu
,
Ruiqi Liu
,
Shiwen Fu
,
Lianxu Shi
,
Chunxia Chen
,
Jinsong Peng
We are grateful for financial support from the Natural Science Foundation of Heilongjiang Province (ZD2021C001, LH2022B003), the National­ Natural Science Foundation of China (32370413), and the Fundamental Research Funds for the Central Universities (2572023CT12).


Abstract

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.

Supporting Information



Publication History

Received: 21 February 2024

Accepted after revision: 22 April 2024

Accepted Manuscript online:
22 April 2024

Article published online:
03 June 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
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  • References

  • 1 Yu Y, Lu WF, Yang ZJ, Wang N, Yu XQ. Bioorg. Chem. 2020; 107: 104534
  • 2 Tafti AD, Mirjalili BB. F, Salehi N, Bamoniri A. J. Iran. Chem. Soc. 2022; 19: 4377
  • 3 Hiyoshi H, Goto N, Tsuchiya M, Lida K, Nakajima Y, Hirata N, Kanda Y, Nagasawa K, Yanagisawa J. Sci. Rep. 2014; 4: 7095
  • 4 Nayak SG, Poojar B. Heliyon 2019; 8: 2318
  • 5 El-Gohary NS, Shaaban MI. Med. Chem. Res. 2013; 1: 287
  • 6 Pejchal V, Pejchalová M, Růžičková Z. Med. Chem. Res. 2015; 24: 3660
  • 7 Cano NH, Ballari MS, López AG, Santiago AN. J. Agric. Food Chem. 2015; 14: 3681
  • 8 Malik S, Bahare RS, Khan SA. Eur. J. Med. Chem. 2013; 67: 1
  • 9 Sahu PK, Sahu PK, Samadhiya P, Sahu PL, Agarwal DD. Med. Chem. Res. 2016; 8: 1551
  • 10 Gabr MT, El-Gohary NS, El-Bendary ER, El-Kerdawy MM. Med. Chem. Res. 2014; 2: 860
  • 11 Chen XP, Hou KQ, Zhou F, Chan AS. C, Xiong XF. J. Org. Chem. 2021; 86: 1667
  • 12 Azzam RA, Osman RR, Elgemeie GH. ACS Omega 2020; 5: 1640
    • 13a Zhang Z, Wang Z, Li Z. Org. Lett. 2022; 24: 5491
    • 13b Anand K, Khan FI, Singh T, Elumalai P, Balakumar C, Premnath D, Lai D, Chuturgoon AA, Saravanan M. ACS Omega 2020; 5: 17973
  • 14 Edmondson SD, Mastracchio A, Parmee ER. Org. Lett. 2000; 2: 1109
  • 15 Yue Y, Chao J, Wang Z, Yang Y, Ye Y, Sun C, Gou X, Liu J. Org. Biomol. Chem. 2021; 19: 7156
    • 16a Barluenga J, Jiménez-Aquino A, Valdés C, Aznar F. Angew. Chem. Int. Ed. 2007; 46: 1529
    • 16b Barluenga J, Jiménez-Aquino A, Aznar F, Valdés C. J. Am. Chem. Soc. 2009; 131: 4031
  • 17 Ackermann L, Althammer A. Angew. Chem. Int. Ed. 2007; 46: 1627
  • 18 Hostyn S, Van Baelen G, Lemière GL. F, Maes BU. W. Adv. Synth. Catal. 2008; 350: 2653
  • 19 Laha JK, Petrou P, Cuny GD. J. Org. Chem. 2009; 74: 3152
  • 20 Jensen T, Pedersen H, Bang-Andersen B, Madsen R, Jørgensen M. Angew. Chem. Int. Ed. 2008; 47: 888
  • 21 Chen X, Lin J, Wang B, Tian X. Org. Lett. 2020; 22: 7704
    • 22a Chen C, Shang G, Zhou J, Yu Y, Li B, Peng J. Org. Lett. 2014; 16: 1872
    • 22b Wang H, Chen C, Huang Z, Yao L, Li B, Peng J. Synthesis 2015; 47: 2457
    • 22c Yu Y, Yue Y, Wang D, Li X, Chen C, Peng J. Synthesis 2016; 48: 3941
    • 22d Li X, Song Z, Chen X, Cai Y, Liu Y, Chen C, Peng J. Chin. J. Org. Chem. 2020; 40: 950
  • 23 Liu J, Zhang Y, Yue Y, Wang Z, Shao H, Zhou K, Lv Q, Zhang Z. J. Org. Chem. 2019; 84: 12946
  • 24 Yue Y, Shao H, Wang Z, Wang K, Wang L, Zhou K, Liu J. J. Org. Chem. 2020; 85: 11265
    • 25a Kappe CO. Acc. Chem. Res. 2000; 12: 879
    • 25b Chandravarkar A, Aneeja T, Anilkumar G. J. Heterocyclic Chem. 2024; 61: 5
  • 27 Li W, Lam Y. J. Comb. Chem. 2005; 7: 721