Synthesis, Table of Contents Synthesis 2024; 56(13): 2005-2014DOI: 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 ∗ Recommend Article Abstract Buy Article All articles of this category 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. Key words Key wordspalladium catalysis - annulation - C–S bond formation - C–N bond formation - o-dihaloarenes - pyrimidobenzothiazoles Full Text References 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 26a Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338 26b Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27 27 Li W, Lam Y. J. Comb. Chem. 2005; 7: 721 Supplementary Material Supplementary Material Supporting Information
