Synthesis 2016; 48(23): 4246-4252
DOI: 10.1055/s-0035-1562788
paper
© Georg Thieme Verlag Stuttgart · New York

Ultrasound-Promoted Synthesis of 4-Pyrimidinols and Their Tosyl Derivatives

Matías Vidal
Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O’Higgins 3363, Santiago, Chile   eMail: moises.dominguez@usach.cl
,
Macarena García-Arriagada
Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O’Higgins 3363, Santiago, Chile   eMail: moises.dominguez@usach.cl
,
Marcos Caroli Rezende
Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O’Higgins 3363, Santiago, Chile   eMail: moises.dominguez@usach.cl
,
Moisés Domínguez*
Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O’Higgins 3363, Santiago, Chile   eMail: moises.dominguez@usach.cl
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 15. Juni 2016

Accepted after revision: 27. Juni 2016

Publikationsdatum:
17. August 2016 (online)


Abstract

Ultrasound irradiation promoted the cyclocondensation of β-keto esters and amidines in good to excellent yields to form sixteen highly substituted 4-pyrimidinols. Tosylation of these compounds, in another ultrasound-promoted conversion, formed 4-pyrimidyl tosylates in high yields. The use of the developed protocol as an alternative route to 4-arylpyrimidines was illustrated with three examples of the Suzuki–Miyaura cross-coupling of the prepared tosylates with phenylboronic acid.

Supporting Information

 
  • References

  • 1 Eicher T, Hauptmann S, Speicher A. Six-Membered Heterocycles . In The Chemistry of Heterocycles . 2nd ed. Wiley-VCH; Weinheim: 2003: 222-256
  • 2 Duerfeldt AS, Boger DL. J. Am. Chem. Soc. 2014; 136: 2119
    • 3a Granifo J, Gaviño R, Freire E, Baggio R. J. Mol. Struct. 2014; 1063: 102
    • 3b Nishikawa M, Nomoto K, Kume S, Nishihara H. J. Am. Chem. Soc. 2012; 134: 10543
    • 3c Jana A, Konar S, Das K, Ray S, Golen JA, Rheingold AL, Carrella LM, Rentschler E, Mondal TK, Kar SK. Polyhedron 2012; 38: 258
    • 3d Panja A. RSC Adv. 2013; 3: 4954
    • 3e Achelle S, Ple N. Curr. Org. Chem. 2012; 9: 163
    • 4a Pettit GR, Tang Y, Zhang Q, Bourne GT, Arm CA, Leet JE, Knight JC, Pettit RK, Chapuis J.-C, Doubek DL, Ward FJ, Weber C, Hooper JN. A. J. Nat. Prod. 2013; 76: 420
    • 4b Chan F.-Y, Sun N, Neves MA. C, Lam PC.-H, Chung W.-H, Wong L.-K, Chow H.-Y, Ma D.-L, Chan P.-H, Leung Y.-C, Chan T.-H, Abagyan R, Wong K.-Y. J. Chem. Inf. Model. 2013; 53: 2131
    • 5a Odingo J, O’Malley T, Kesicki EA, Alling T, Bailey MA, Early J, Ollinger J, Dalai S, Kumar N, Singh RV, Hipskind PA, Cramer JW, Ioerger T, Sacchettini J, Vickers R, Parish T. Bioorg. Med. Chem. 2014; 22: 6965
    • 5b Grosjean S, Triki S, Meslin J.-C, Julienne K, Deniaud D. Tetrahedron 2010; 66: 9912
    • 5c Russell MG. N, Carling RW, Atack JR, Bromidge FA, Cook SM, Hunt P, Isted C, Lucas M, McKernan RM, Mitchinson A, Moore KW, Narquizian R, Macaulay AJ, Thomas D, Thompson S.-A, Wafford KA, Castro JL. J. Med. Chem. 2005; 48: 1367
    • 5d Yang G, Jia Q, Chen L, Du Z, Wang J. RSC Adv. 2015; 5: 76759
    • 5e Gayon E, Szymczyk M, Gérard H, Vrancken E, Campagne J.-M. J. Org. Chem. 2012; 77: 9205
    • 5f Zhou N, Xie T, Li Z, Xie Z. Chem. Eur. J. 2014; 20: 17311
    • 5g Deibl N, Ament K, Kempe R. J. Am. Chem. Soc. 2015; 137: 12804
    • 5h Zhichkin P, Fairfax DJ, Eisenbeis SA. Synthesis 2002; 720
    • 5i Anderson ED, Boger DL. Org. Lett. 2011; 13: 2492
  • 6 Bera MK, Domínguez M, Hommes P, Reissig H.-U. Beilstein J. Org. Chem. 2014; 10: 394
    • 7a Itami K, Yamazaki D, Yoshida J. J. Am. Chem. Soc. 2004; 126: 15396
    • 7b Schomaker JM, Delia TJ. J. Org. Chem. 2001; 66: 7125
    • 7c Achelle S, Ramondenc Y, Marsais F, Plé N. Eur. J. Org. Chem. 2008; 3129
    • 7d Malik I, Ahmed Z, Reimann S, Ali I, Villinger A, Langer P. Eur. J. Org. Chem. 2011; 2088
    • 7e Achelle S, Ramondenc Y, Dupas G, Plé N. Tetrahedron 2008; 64: 2783
    • 8a Liu Z, Li D, Li S, Bai D, He X, Hu Y. Tetrahedron 2007; 63: 1931
    • 8b Sakamoto T, Kondo Y, Watanabe RY. O, Yamanaka H. Chem. Pharm. Bull. 1986; 34: 2719
    • 9a Kuroda J.-i, Inamoto K, Hiroya K, Doi T. Eur. J. Org. Chem. 2009; 2251
    • 9b Zhang L, Meng T, Wu J. J. Org. Chem. 2007; 72: 9346
  • 10 Yang J, Liu S, Zheng JF, Zhou J. Eur. J. Org. Chem. 2012; 6248
  • 11 Gøgsig TM, Lindhardt AT, Dekhane M, Grouleff J, Skrydstrup T. Chem. Eur. J. 2009; 15: 5950
  • 12 Mahmoodi N, Shoja S, Tabatabaeian K, Sharifzadeh B. Ultrason. Sonochem. 2015; 23: 3136
  • 13 Lockman JW, Klimova Y, Anderson MB, Willardsen JA. Synth. Commun. 2012; 42: 1715
  • 14 Lan Y, Chen Y, Cao X, Zhang J, Wang J, Xu X, Qiu Y, Zhang T, Liu X, Liu B.-F, Zhang G. J. Med. Chem. 2014; 57: 10404
  • 15 Ried W, Lohwasser H. Justus Liebigs Ann. Chem. 1966; 699: 88
  • 16 Negoro K, Yonetoku Y, Misawa-Mukai H, Hamaguchi W, Maruyama T, Yoshida S, Takeuchi M, Ohta M. Bioorg. Med. Chem. 2012; 20: 5235
  • 17 Brown DJ, Hoskins JA. J. Chem. Soc. B 1971; 2214
  • 18 Tetsuzo K, Takuo C, Makoto S. Heterocycles 1981; 16: 577
  • 19 Guan H.-P, Hu Q.-S, Hu C.-M. Synthesis 1996; 997
  • 20 Achelle S, Robin-le Guen F. Tetrahedron Lett. 2013; 54: 4491
  • 21 Kong K.-H, Chen Y, Ma X, Chui WK, Lam Y. J. Comb. Chem. 2004; 6: 928