Palladium-Catalyzed Cross-Coupling of 4-(Tosyloxy)quinazolines with H-Phosphonates and Phosphine Oxides: An Efficient Access to 2-(Hetero)aryl-4-phosphorylated Quinazolines

Abstract

A series of 2-(hetero)aryl-4-phosphorylated quinazolines was successfully synthesized in moderate to excellent yields via a palladium-catalyzed C–O/P–H cross-coupling reaction of 4-(tosyl­oxy)quinazolines with H-phosphonates and phosphine oxides. This efficient and green methodology provides an alternative straightforward protocol for the introduction of phosphorus groups to quinazoline compounds at the C4 position via C–O activation.

Key words

palladium catalysis - 4-(tosyloxy)quinazoline - H-phosphonates - phosphine oxides - 4-phosphorylated quinazolines - cross-coupling

Publication History

Received: 18 July 2021

Accepted after revision: 17 September 2021

Accepted Manuscript online:
17 September 2021

Article published online:
25 October 2021

• References

• 1a Michael JP. Nat. Prod. Rep. 2002; 19: 742
• 1b Chen K, Al Aowad AF, Adelstein SJ, Kassis AI. J. Med. Chem. 2007; 50: 663
• 1c Brunton SA, Stibbard JH. A, Rubin LL, Kruse LI, Guicherit OM, Boyd EA, Price S. J. Med. Chem. 2008; 51: 1108
• 1d Colotta V, Catarzi D, Varano F, Lenzi O, Filacchioni G, Costagli C, Galli A, Ghelardini C, Galeotti N, Gratteri P, Sgrignani J, Deflorian F, Moro S. J. Med. Chem. 2006; 49: 6015
• 2a Michael JP. Nat. Prod. Rep. 1999; 16: 697
• 2b Michael JP. Nat. Prod. Rep. 2003; 20: 476
• 3a Chappie TA, Humphrey JM, Allen MP, Estep KG, Fox CB, Lebel LA, Liras S, Marr ES, Menniti FS, Pandit J, Schmidt CJ, Tu MH, Williams RD, Yang FV. J. Med. Chem. 2007; 50: 182
• 3b Zhang JT, Zhu DP, Yu CM, Wang CF, Wang ZY. Org. Lett. 2010; 12: 2841
• 3c Sirisoma N, Pervin A, Zhang H, Jiang SC, Willardsen JA, Anderson MB, Mather G, Pleiman CM, Kasibhatla S, Tseng B, Drewe J, Cai SX. J. Med. Chem. 2009; 52: 2341
• 3d Witt A, Bergman J. Curr. Org. Chem. 2003; 7: 659
• 4a Shreder KR, Wong MS, Nomanbhoy T, Leventhal PS, Fuller SR. Org. Lett. 2004; 6: 3715
• 4b Nakamura H, Onagi S. Tetrahedron Lett. 2006; 47: 2539
• 4c Wan ZK, Wacharasindhu S, Levins CG, Lin M, Tabei K, Mansour TS. J. Org. Chem. 2007; 72: 10194
• 4d Wan ZK, Wacharasindhu S, Binnun E, Mansour T. Org. Lett. 2006; 8: 2425
• 4e Wacharasindhu S, Bardhan S, Wan ZK, Tabei K, Mansour TS. J. Am. Chem. Soc. 2009; 131: 4174
• 4f Connolly DJ, Lacey PM, McCarthy M, Saunders CP, Carroll AM, Goddard R, Guiry PJ. J. Org. Chem. 2004; 69: 6572
• 4g Rewcastle GW, Denny WA, Bridges AJ, Zhou HR, Cody DR, McMichael A, Fry DW. J. Med. Chem. 1995; 38: 3482
• 5a Peng YY, Qiu GY. S, Yang Q, Yuan JJ, Deng ZH. Synthesis 2012; 44: 1237
• 5b Qiu GY. S, Huang P, Yang Q, Lu H, Xu JS, Deng ZH, Zhang M, Peng YY. Synthesis 2013; 45: 3131
• 5c Zhao X, Zhou YR, Yang Q, Xie YP, Ding QP, Deng ZH, Zhang M, Xu JS, Peng YY. Synthesis 2013; 45: 3245
• 5d Peng YY, Huang P, Wang Y, Zhou YR, Yuan JJ, Yang Q, Jiang X, Deng ZH, Xu JS. Org. Biomol. Chem. 2014; 12: 5922
• 5e Chen X, Yang Q, Zhou YR, Deng ZH, Mao XC, Peng YY. Synthesis 2015; 47: 2055
• 5f Ye XL, Yuan ZH, Zhou YR, Yang Q, Xie YP, Deng ZH, Peng YY. J. Heterocycl. Chem. 2016; 53: 1956
• 5g Ye XL, Yuan JJ, Zhou YR, Deng ZH, Mao XC, Peng YY. Synthesis 2016; 48: 3976
• 5h Ye XL, Huang J, Deng ZH, Yuan JJ, Peng YY. Synthesis 2021; 53: 383
• 6a Wéber C, Bielik A, Szendrei GI, Greiner I. Tetrahedron Lett. 2002; 43: 2971
• 6b Kanuma K, Omodera K, Nishiguchi M, Funakoshi T, Chaki S, Semple G, Tran TA, Kramer B, Hsu D, Casper M, Thomsen B, Beeley N, Sekiguchi Y. Bioorg. Med. Chem. Lett. 2005; 15: 2565
• 6c Rachid Z, Brahimi F, Qiu QY, Williams C, Hartaley JM, Hartaley JA, Jean-Claude BJ. J. Med. Chem. 2007; 50: 2605
• 6d Murai M, Sekiguchi K, Nishioka T, Miyoshi H. Biochemistry 2009; 48: 688
• 6e Gomtsyan A, Bayburt EK, Schmidt RG, Zheng GZ, Perner RJ, Didomenico S, Koenig JR, Turner S, Jinkerson T, Drizin I, Hannick SM, Macri BS, McDonald HA, Honore P, Wismer CT, Marsh KC, Wetter J, Stewart KD, Oie T, Jarvis MF, Surowy CS, Faltynek CR, Lee CH. J. Med. Chem. 2005; 48: 744
• 7a Choy PY, Chung KH, Yang QJ, So CM, Sun RW. Y, Kwong FY. Chem. Asian J. 2018; 13: 2465
• 7b Xie XM, Ni G, Ma FF, Ding LN, Xu S, Zhang ZG. Synlett 2011; 955
• 7c Mantel ML. H, Lindhardt AT, Lupp D, Skydstrup T. Chem. Eur. J. 2010; 16: 5437
• 7d Ogata T, Hartwig JF. J. Am. Chem. Soc. 2008; 130: 13848
• 7e Jiang J, Zhu HB, Shen YJ, Tu T. Org. Chem. Front. 2014; 1: 1172
• 7f Kampmann SS, Sobolev AN, Koutsantonis GA, Stewart SG. Adv. Synth. Catal. 2014; 356: 1967
• 7g Iglesias MJ, Blandez JF, Fructos MR, Prieto A, Álvarez E, Belderrain TR, Nicasio MC. Organometallics 2012; 31: 6312

For some representative examples, see:
• 8a Inoue A, Shinokubo H, Oshima K. J. Am. Chem. Soc. 2003; 125: 1484
• 8b Smith RC, Protasiewicz JD. J. Am. Chem. Soc. 2004; 126: 2268
• 8c Tang WJ, Zhang XM. Chem. Rev. 2003; 103: 3029
• 8d Wydysh EA, Medghalchi SM, Vadlamudi A, Townsend CA. J. Med. Chem. 2009; 52: 3317
• 8e Sivendran S, Jones V, Sun D, Wang Y, Grzegorzewicz AE, Scherman MS, Napper AD, McCammon JA, Lee RE, Diamond SL, McNeil M. Bioorg. Med. Chem. 2010; 18: 896
• 8f Steininger H, Schuster M, Kreuer KD, Kaltbeitzel A, Bingöl B, Meyer WH, Schauff S, Brunklaus G, Maier J, Spiess HW. Phys. Chem. Chem. Phys. 2007; 9: 1764
• 8g Bock T, Möhwald H, Mülhaupt R. Macromol. Chem. Phys. 2007; 208: 1324
• 9a Westheimer FH. Science 1987; 235: 1173
• 9b Seto H, Kuzuyama T. Nat. Prod. Rep. 1999; 16: 589
• 9c Kafarski P, Lejczak B. Curr. Med. Chem.: Anti-Cancer Agents 2001; 1: 301
• 9d Mader MM, Bartlett PA. Chem. Rev. 1997; 97: 1281
• 9e Kafarski P, Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991; 63: 193
• 9f Zon G. Prog. Med. Chem. 1982; 19: 205
• 10a Alexandre FR, Amador A, Bot S, Caillet C, Convard T, Jakubik J, Musiu C, Poddesu B, Vargiu L, Liuzzi M, Roland A, Seifer M, Standring D, Storer R, Dousson CB. J. Med. Chem. 2011; 54: 392
• 10b Storer R, Dousson C, Alexandre FR, Roland A. WO PCT Int. Appl 054182, 2006
• 10c LaRegina G, Coluccia A, Silvestri R. Antiviral Chem. Chemother. 2010; 20: 213
• 11 Li XS, Zhang DW, Pang H, Shen F, Fu H, Jiang YY, Zhao YF. Org. Lett. 2005; 7: 4919
• 12a Li ZJ, Fan FH, Zhang ZY, Xiao YX, Liu D, Liu ZQ. RSC Adv. 2015; 5: 27853
• 12b Zhang HL, Gu ZX, Li ZY, Pan CD, Li WP, Hu HW, Zhu CJ. J. Org. Chem. 2016; 81: 2122
• 12c Hua HL, Zhang BS, He YT, Qiu YF, Wu XX, Xu PF, Liang YM. Org. Lett. 2016; 18: 216
• 12d Pan XQ, Zou JP, Zhang GL, Zhang W. Chem. Commun. 2010; 46: 1721
• 12e Pan XQ, Wang L, Zou JP, Zhang W. Chem. Commun. 2011; 47: 7875
• 12f Li YM, Sun M, Wang HL, Tian QP, Yang SD. Angew. Chem. Int. Ed. 2013; 52: 3972
• 12g Zhang CW, Li ZD, Zhu L, Yu LM, Wang ZT, Li CZ. J. Am. Chem. Soc. 2013; 135: 14082
• 12h Chu XQ, Zi Y, Meng H, Xu XP, Ji SJ. Chem. Commun. 2014; 50: 7642
• 12i Unoh Y, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2013; 52: 12975
• 12j Chen YR, Duan WL. J. Am. Chem. Soc. 2013; 135: 16754
• 12k Li DP, Pan XQ, An LT, Zou JP, Zhang W. J. Org. Chem. 2014; 79: 1850
• 12l Feng CG, Ye MC, Xiao KJ, Li SH, Yu JQ. J. Am. Chem. Soc. 2013; 135: 9322
• 12m Xu J, Zhang PB, Gao YZ, Chen YY, Tang G, Zhao YF. J. Org. Chem. 2013; 78: 8176
• 12n Xue QC, Xie J, Jin HM, Cheng YX, Zhu CJ. Org. Biomol. Chem. 2013; 11: 1606
• 12o Yang B, Yang TT, Li XA, Wang JJ, Yang SD. Org. Lett. 2013; 15: 5024
• 12p Wu YL, Liu LL, Yan KL, Xu PX, Gao YX, Zhao YF. J. Org. Chem. 2014; 79: 8118
• 12q Wang T, Sang S, Liu LL, Qiao HW, Gao YX, Zhao YF. J. Org. Chem. 2014; 79: 608
• 13a Gooβen LJ, Dezfuli MK. Synlett 2005; 3: 445
• 13b Bessmertnykh A, Douaihy CM, Muniappan S, Guilard R. Synthesis 2008; 10: 1575
• 13c Yang J, Xiao J, Chen TQ, Han LB. J. Org. Chem. 2016; 81: 3911
• 13d Kalek M, Jezowska M, Stawinski J. Adv. Synth. Catal. 2009; 351: 3207
• 13e Deal EL, Petit C, Montchamp JL. Org. Lett. 2011; 13: 3270
• 13f Kalek M, Stawinski J. Organometallics 2007; 26: 5840
• 13g Demmer CS, Krogsgaard-Larsen N, Bunch L. Chem. Rev. 2011; 111: 7981
• 13h Xu YY, Zhang J. Tetrahedron Lett. 1985; 26: 4771
• 13i Bloomfield AJ, Herzon SB. Org. Lett. 2012; 14: 4370
• 13j Liu L, Wang YL, Zeng ZP, Xu PX, Gao YX, Yin YW, Zhao YF. Adv. Synth. Catal. 2013; 355: 659
• 14 Hirao T, Masunaga T, Ohshiro Y, Agawa T. Tetrahedron Lett. 1980; 21: 3595
• 15a Hirao T, Masunaga T, Ohshiro Y, Agawa T. Synthesis 1981; 56
• 15b Gelman D, Jiang L, Buchwald SL. Org. Lett. 2003; 5: 2315
• 15c Huang C, Tang X, Fu H, Jiang YY, Zhao YF. J. Org. Chem. 2006; 71: 5020
• 15d Heinicke J, Gupta N, Surana A, Peulecke N, Witt B, Steinhauser K, Bansal RK, Jones PG. Tetrahedron 2001; 57: 9963
• 15e Yao Q, Levchik S. Tetrahedron Lett. 2006; 47: 277
• 15f Rao HH, Jin Y, Fu H, Jiang YY, Zhao YF. Chem. Eur. J. 2006; 12: 3636
• 15g Kohler MC, Sokol JG, Stockland RA. Jr. Tetrahedron Lett. 2009; 50: 457
• 15h Zhang XH, Liu HZ, Hu XM, Tang G, Zhu J, Zhao YF. Org. Lett. 2011; 13: 3478
• 15i Kalek M, Stawinski J. Organometallics 2008; 27: 5876
• 15j Belabassi Y, Alzghari S, Montchamp JL. J. Organomet. Chem. 2008; 693: 3171
• 15k Berger O, Petit C, Deal EL, Montchamp JL. Adv. Synth. Catal. 2013; 355: 1361
• 15l Xu K, Yang F, Zhang GD, Wu YJ. Green Chem. 2013; 15: 1055
• 15m Schwan AL. Chem. Soc. Rev. 2004; 33: 218
• 16a Lu XY, Zhu JY. Synthesis 1987; 726
• 16b Kurz L, Lee G, Morgans DJr, Waldyke MJ, Ward T. Tetrahedron Lett. 1990; 31: 6321
• 16c Brück A, Ruhland K. Organometallics 2009; 28: 6383
• 17a Holt DA, Erb JM. Tetrahedron Lett. 1989; 30: 5393
• 17b Kalek M, Ziadi A, Stawinski J. Org. Lett. 2008; 10: 4637
• 18a Fu WC, So CM, Kwong FY. Org. Lett. 2015; 17: 5906
• 18b Liao LL, Gui YY, Zhang XB, Shen G, Liu HD, Zhou WJ, Li J, Yu DG. Org. Lett. 2017; 19: 3735
• 18c Yang CT, Han J, Liu J, Li Y, Zhang F, Gu M, Hu S, Wang XL. RSC Adv. 2017; 7: 24652
• 18d Shen CR, Yang GQ, Zhang WB. Org. Biomol. Chem. 2012; 10: 3500
• 18e Li C.-J. Russ. J. Gen. Chem. 2020; 90: 725
• 19 Issleib K, Abicht H.-P. J. Prakt. Chem. 1973; 315: 649