Synlett 2012; 23(14): 2137-2141
DOI: 10.1055/s-0031-1290433
letter
© Georg Thieme Verlag Stuttgart · New York

A Novel and Highly Regioselective Route to Construct Methylthio-Substituted Pyridazines from Aryl Methyl Ketones at Room Temperature

Liuming Wu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67867773   Email: chwuax@mail.ccnu.edu.cn
,
Yan Yang
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67867773   Email: chwuax@mail.ccnu.edu.cn
,
Meng Gao
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67867773   Email: chwuax@mail.ccnu.edu.cn
,
Dongxue Zhang
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67867773   Email: chwuax@mail.ccnu.edu.cn
,
Wenming Shu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67867773   Email: chwuax@mail.ccnu.edu.cn
,
Yanping Zhu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67867773   Email: chwuax@mail.ccnu.edu.cn
,
Anxin Wu*
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67867773   Email: chwuax@mail.ccnu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 18 May 2012

Accepted after Revision: 12 June 2012

Publication Date:
03 August 2012 (online)


Abstract

A novel and highly regioselective two-step homocoupling/cyclization procedure from easily available aryl methyl ketones and hydrazine hydrate was developed for the synthesis of methylthio-substituted pyridazines at room temperature. The method has remarkable advantages owing to the simple substrates, mild reaction conditions, ease of manipulation, good yields and high ­regioselectivity.

Supporting Information

Primary Data

 
  • References

  • 1 Tucker JA, Allwine DA, Grega KC, Barbachyn MR, Klock JL, Adamski JL, Brickner SJ, Hutchinson DK, Ford CW, Zurenko GE, Conradi RA, Burton PS, Jensen RM. J. Med. Chem. 1998; 41: 3727
  • 2 Rohet F, Rubat C, Coudert P, Couquelet J. Bioorg. Med. Chem. 1997; 5: 655
  • 3 Benson SC, Palabrica CA, Snyder JK. J. Org. Chem. 1987; 52: 4610
  • 4 Tamayo N, Liao L, Goldberg M, Powers D, Tudor YY, Yu V, Wong LM, Henkle B, Middleton S, Syed R, Harvey T, Jang G, Hungate R, Dominguez C. Bioorg. Med. Chem. Lett. 2005; 15: 2409
  • 5 Naud S, Pipelier M, Viault G, Adjou A, Huet F, Legoupy S, Aubertin AM, Evain M, Dubreuil D. Eur. J. Org. Chem. 2007; 3296
  • 6 Cuccia LA, Lehn J.-M, Homo J.-C, Schmutz M. Angew. Chem. Int. Ed. 2000; 39: 233
    • 7a Marriner GA, Garner SA, Jang H.-Y, Krische MJ. J. Org. Chem. 2004; 69: 1380
    • 7b Yang XY, Knochel P. Org. Lett. 2006; 8: 1941
    • 8a Maes BU. W, Lemière GL. F, Dommisse R, Augustyns K, Haemers A. Tetrahedron 2000; 56: 1777
    • 8b Song CJ, Zhao P, Liu Y, Liu H, Li WJ, Shi S, Chang JB. Tetrahedron 2010; 66: 5378
  • 9 Attanasi OA, Favi G, Filippone P, Perrulli FR, Santeusanio S. Org. Lett. 2009; 11: 309
  • 10 Al Dulayymi AR, Baird MS. Tetrahedron 1998; 54: 12897
    • 11a Hamasaki A, Ducray R, Boger DL. J. Org. Chem. 2006; 71: 185
    • 11b Xie HX, Zu LS, Oueis HR, Li H, Wang J, Wang W. Org. Lett. 2008; 10: 1923
    • 11c Helm MD, Moore JE, Plant A, Harrity JP. A. Angew. Chem. Int. Ed. 2005; 44: 3889
    • 11d Mann E, Moisan L, Hou JL, Rebek J. Tetrahedron Lett. 2008; 49: 903
  • 12 Rykowski A, Woliñska E. Tetrahedron Lett. 1996; 37: 5795
    • 13a Minetto G, Lampariello LR, Taddei M. Synlett 2005; 2743
    • 13b Raghavan S, Anuradha K. Synlett 2003; 711
    • 13c Altomare C, Cellamare S, Summo L, Catto M, Carotti A. J. Med. Chem. 1998; 41: 3812
  • 14 Flögel O, Reißig HU. Eur. J. Org. Chem. 2004; 2797
  • 15 Nakayama J, Konishi T, Ishii A, Hoshino M. Bull. Chem. Soc. Jpn. 1989; 62: 2608
    • 16a Cermola F, Iesce MR, Buonerba G. J. Org. Chem. 2005; 70: 6503
    • 16b Nakayama J, Hasemi R, Yoshimura K, Sugihara Y, Yamaoka S. J. Org. Chem. 1998; 63: 4912
    • 16c South MS, Jakuboski TL, Westmeyer MD, Dukesherer DR. J. Org. Chem. 1996; 61: 8921
    • 16d Supurgibekov MB, Zakharova VM, Sieler J, Nikolaev VA. Tetrahedron 2011; 52: 341
    • 17a Bluth R. Pharmazie 1982; 37: 136
    • 17b Bluth R. Pharmazie 1982; 37: 208
    • 17c Bluth R. Pharmazie 1981; 36: 775
    • 18a Leprêtre A, Turck A, Plé N, Quéguiner G. Tetrahedron 2000; 56: 3709
    • 18b Berghian C, Darabantu M, Turck A, Plé N. Tetrahedron 2005; 61: 9637
    • 18c Leprêtre A, Turck A, Plé N, Knochel P, Quéguiner G. Tetrahedron 2000; 56: 265
    • 18d Sayah M, Organ MG. Chem. Eur. J. 2011; 17: 11719
    • 18e Ali A, Cablewski T, Francis CL, Ganguly AK, Sargent RM, Sawutz DG, Winzenberg KN. Bioorg. Med. Chem. Lett. 2011; 21: 4160
    • 18f Abbot SC, Billedeau RJ, Dewdney NJ, Gabriel T, Goldstein DM, McCaleb KL, Soth M, Trejo-Martin TA, Zecic H. Heterocycles 2009; 78: 2811
    • 18g Sauer J, Heldmann DK, Hetzenegger J, Krauthan J, Sichert H, Schuster J. Eur. J. Org. Chem. 1998; 2885
    • 18h Boger DL, Sakya SM. J. Org. Chem. 1988; 53: 1415
    • 18i Sitamze JM, Schmitt M, Wermuth CG. J. Org. Chem. 1992; 57: 3257
    • 18j Hamasaki A, Ducray R, Boger DL. J. Org. Chem. 2006; 71: 185
  • 19 Barbier P. C. R. Acad. Sci. Paris 1899; 128: 100
    • 20a Yin GD, Zhou BH, Meng XG, Wu AX, Pan YJ. Org. Lett. 2006; 8: 2245
    • 20b Yin GD, Wang ZH, Chen AH, Gao M, Wu AX, Pan YJ. J. Org. Chem. 2008; 73: 3377

      For selected examples, see:
    • 21a Capon RJ, Stewart M, Ratnayake R, Lacey E, Gill JH. J. Nat. Prod. 2007; 70: 1746
    • 21b Carroll AR, Avery VM. J. Nat. Prod. 2009; 72: 696
    • 21c El-Gamal AA, Wang WL, Duh CY. J. Nat. Prod. 2005; 68: 815
    • 21d Li GY, Li BG, Yang T, Yan JF, Liu GY, Zhang GL. J. Nat. Prod. 2006; 69: 1374
    • 21e Blanchard P, Jousselme B, Frère P, Roncali J. J. Org. Chem. 2002; 67: 3961
    • 21f Reddinger JL, Reynolds JR. J. Org. Chem. 1996; 61: 4833
    • 21g Kobayashi K, Masu H, Shuto A, Yamaguchi K. Chem. Mater. 2005; 17: 6666
    • 21h Enoki T, Miyazaki A. Chem. Rev. 2004; 104: 5449
    • 21i Forgie JC, Kanibolotsky AL, Skabara PJ, Coles SJ, Hursthouse MB, Harriington RW, Clegg W. Macromolecules 2009; 42: 2570
    • 21j Arroyo IJ, Hu RR, Merino G, Tang BZ, Pena-Cabrera E. J. Org. Chem. 2009; 74: 5719
    • 22a Boger DL, Sakya SM. J. Org. Chem. 1988; 53: 1415
    • 22b Hamasaki A, Ducray R, Boger DL. J. Org. Chem. 2006; 71: 185
    • 23a Deng C, Yang Y, Gao M, Zhu YP, Wu AX, Ma JR, Yin GD. Tetrahedron 2012; 68: 3828
    • 23b Goel A, Singh FV, Verma D. Synlett 2005; 2027
    • 23c Ram VJ, Agarwal N. Tetrahedron Lett. 2001; 42: 7127
    • 23d Singh FV, Kumar V, Kumar B, Goel A. Tetrahedron 2007; 63: 10971
    • 24a Takei H, Miura M, Sugimura H, Okamura H. Chem. Lett. 1979; 8: 1447
    • 24b Mehta VP, Sharma A, Van der Eycken E. Org. Lett. 2008; 10: 1147
    • 24c Begouin JM, Rivard M, Gosmini C. Chem. Commun. 2010; 5972
    • 24d Pellegatti L, Vedrenne E, Leger JM, Jarry C, Router S. Synlett 2009; 2137
  • 25 Misra NC, Ila H. J. Org. Chem. 2010; 75: 5195
  • 26 Sanz R, Guilarte V, Hernando E, Sanjuacn AM. J. Org. Chem. 2010; 75: 7443
  • 27 Crystal structure data for compound 3a: CCDC number 879829, C17H14N2S, monoclinic, space group P2(1)/c, a = 7.5731(11), b = 18.470(3), c = 20.894(3) Å, α = 90°, β = 95.706(2)°, γ = 90°, V = 2908.1(7) Å3, T = 298(2) K, Z = 8, DC = 1.272 Mg/m3, μ = 0.213 mm–1, λ = 0.71073 Å, F(000) 1168, crystal size 0.16 × 0.12 × 0.10 mm3, 5106 independent reflections [R(int) = 0.0356], reflections collected 16948, refinement method: Full-matrix least-squares on F2: goodness-of-fit on F2 1.386, final R indices [I >2σ(I)], R1 = 0.0912, wR2 = 0.1725, largest diff. peak and hole 0.320 and –0.237 e.Å–3.
  • 28 Crystal structure data for compound 4a: CCDC number 879830, C17H14N2OS, monoclinic, space group P2(1)/c, a = 9.899(2), b = 20.194(5), c = 7.881(2) Å, α = 90°, β = 111.832(4)°, γ = 90°, V = 1462.5(6) Å3, T = 296(2) K, Z = 4, DC = 1.337 Mg/m3, μ = 0.221 mm–1, λ = 0.71073 Å, F(000) 616, crystal size 0.20 × 0.10 × 0.10 mm3, 3175 independent reflections [R(int) = 0.0305], reflections collected 10377, refinement method: Full-matrix least-squares on F2: goodness-of-fit on F2 1.066, final R indices [I >2σ(I)], R1 = 0.0420, wR2 = 0.1189, largest diff. peak and hole 0.386 and –0.227 e.Å–3