Synthesis 2018; 50(20): 4133-4139
DOI: 10.1055/s-0037-1610444
paper
© Georg Thieme Verlag Stuttgart · New York

2-Trifluoromethyl-1,3-diazabutadienes as Useful Intermediates for the Construction of 2-Trifluoromethylpyrimidine Derivatives

Ignacio Medina-Mercado
a   Departamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Toluca, C.P. 50180, México   Email: mromeroo@uaemex.mx
,
Ivann Zaragoza-Galicia
a   Departamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Toluca, C.P. 50180, México   Email: mromeroo@uaemex.mx
,
b   Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, IA 52242, USA
,
Moisés Romero-Ortega*
a   Departamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Toluca, C.P. 50180, México   Email: mromeroo@uaemex.mx
› Author Affiliations
The Consejo Nacional de Ciencia y Tecnologia is gratefully acknowledged for providing a M.Sc. fellowship to Ignacio Medina (CONACyT 581817 and grant S-26659).
Further Information

Publication History

Received: 04 May 2018

Accepted after revision: 02 June 2018

Publication Date:
16 July 2018 (online)


Abstract

A methodology to prepare 2-trifluoromethylpyrimidines has been developed on the basis of a cyclization reaction of 2-trifluoromethyl-1,3-diazabutadienes. These 2-trifluoromethyl-1,3-diazabutadienes were prepared by the condensation of trifluoroacetamidine and amide acetals or with chloromethaniminium salt derived from N,N-dimethylbenzamide with phosphorus oxychloride. The cycloaddition reactions of these 2-trifluoromethyl-1,3-diazabutadienes with DMAD and phenylacetyl chloride provided 2-trifluoromethylpyrimidine derivatives in regular to moderate overall yield.

Supporting Information

 
  • References

  • 1 Smart BE. J. Fluorine Chem. 2001; 109: 3
    • 2a Harsanyi A. Sandford G. Green Chem. 2015; 17: 2081
    • 2b Purser S. Moore PR. Swallow S. Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
    • 2c Hagmann WK. J. Med. Chem. 2008; 51: 4359
    • 2d Kirk KL. J. Fluorine Chem. 2006; 127: 1013
    • 2e Salas PF. Herrmann C. Orvig C. Chem. Rev. 2013; 113: 3450
  • 3 Wiehn MS. Vinogradova EV. Togni A. J. Fluorine Chem. 2010; 131: 951
  • 4 Alonso C. Martínez De Marigorta E. Rubiales G. Palacios F. Chem. Rev. 2015; 115: 1847
  • 5 Liang T. Neumann CN. Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214
  • 6 Zhu W. Wang J. Wang S. Gu Z. Aceña JL. Izawa K. Liu H. Soloshonok VA. J. Fluorine Chem. 2014; 167: 37
  • 7 Ma JA. Cahard D. J. Fluorine Chem. 2007; 128: 975
  • 8 Barone JA. Peters E. Tieckelmann H. J. Org. Chem. 1959; 24: 198
  • 9 Inoue S. Saggiomo AJ. Nodiff EA. J. Org. Chem. 1961; 26: 4504
  • 10 Kawase M. Hirabayashi M. Salto S. Yamamoto K. Tetrahedron Lett. 1999; 40: 2541
  • 11 Soufyane M. Mirand C. Lévy J. Tetrahedron Lett. 1993; 34: 7737
  • 12 Mirand C. Soufyane M. van den Broek S. Khamliche L. Heterocycles 1999; 51: 2445
  • 13 Berber H. Soufyane M. Mirand C. Schmidt S. Aubertin AM. Tetrahedron 2001; 57: 7369
  • 14 Berber H. Soufyane M. Santillana-Hayat M. Mirand C. Tetrahedron Lett. 2002; 43: 9233
  • 15 Ondi L. Lefebvre O. Schlosser M. Eur. J. Org. Chem. 2004; 3714
  • 16 Takahashi M. Akiyama K. Suzuki T. Inoue H. J. Heterocycl. Chem. 2008; 45: 601
  • 17 Sukach VA. Tkachuk VM. Rusanov EB. Röschenthaler GV. Vovk MV. Tetrahedron 2012; 68: 8408
  • 18 Boger DL. Tetrahedron 1983; 39: 2869
  • 19 Jayakumar S. Ishar MP. S. Mahajan MP. Tetrahedron 2002; 58: 379
  • 20 Matsuda I. Yamamoto S. Ishii Y. J. Chem. Soc., Perkin Trans. 1 1976; 1528
  • 21 Mazumdar SN. Mukherjee S. Sharma AK. Sengupta D. Mahajan MP. Tetrahedron 1994; 50: 7579
  • 22 Barluenga J. Tomás M. Ballesteros A. López LA. Tetrahedron Lett. 1989; 30: 4573
  • 23 Sain B. Singh SP. Sandhu JS. Tetrahedron 1992; 48: 4567
  • 24 Abbiati G. Cirrincione de Carvalho A. Rossi E. Tetrahedron 2003; 59: 7397
  • 25 Guzmán A. Romero M. Talamás FX. Villena R. Greenhouse R. Muchowski JM. J. Org. Chem. 1996; 61: 2470
  • 26 Seballos-Resendiz A. Lechuga-Eduardo H. Barroso-Flores J. Martinez-Otero D. Romero-Ortega M. Synthesis 2016; 48: 2205
  • 27 Lechuga-Eduardo H. Olivo HF. Romero-Ortega M. Eur. J. Org. Chem. 2014; 5910
  • 28 Husted D. U.S. Patent 2 676 985, 1954
  • 29 Reilly WL. Brown HC. J. Am. Chem. Soc. 1956; 78: 6032
  • 30 Barone JA. Peters E. Tieckelmann H. J. Org. Chem. 1959; 24: 198
  • 31 Moss RA. Guo W. Denney DZ. Houk KN. Rondanlb NG. J. Am. Chem. Soc. 1981; 103: 6164
  • 32 Bredereck H. Effenberger H. Beyerlin F. Chem. Ber. 1964; 97: 3081