Synthesis 2013; 45(23): 3281-3287
DOI: 10.1055/s-0033-1339763
paper
© Georg Thieme Verlag Stuttgart · New York

The Activity of Magnesium/Aluminum ‘Memory Effect’ Reconstructed Hydrotalcites in the Microwave-Assisted Synthesis of 2-Benzimidazolethiol and Its Alkylated Derivatives

Deysi Y. Cruz-Gonzalez
a   Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana-Azcapotzalco, Av. San Pablo 180, C.P. 02200 México D.F., México   Fax: +52(55)53189000   Email: gns@correo.azc.uam.mx
,
Rodrigo González-Olvera
a   Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana-Azcapotzalco, Av. San Pablo 180, C.P. 02200 México D.F., México   Fax: +52(55)53189000   Email: gns@correo.azc.uam.mx
,
Deyanira Angeles-Beltrán
a   Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana-Azcapotzalco, Av. San Pablo 180, C.P. 02200 México D.F., México   Fax: +52(55)53189000   Email: gns@correo.azc.uam.mx
,
Guillermo E. Negrón-Silva*
a   Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana-Azcapotzalco, Av. San Pablo 180, C.P. 02200 México D.F., México   Fax: +52(55)53189000   Email: gns@correo.azc.uam.mx
,
Rosa Santillan
b   Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000 México D.F., México
› Author Affiliations
Further Information

Publication History

Received: 18 July 2013

Accepted after revision: 19 August 2013

Publication Date:
27 September 2013 (online)


Abstract

An efficient and practical methodology for the microwave-assisted synthesis of 2-benzimidazolethiol from 1,2-benzenediamine and carbon disulfide using reconstructed hydrotalcite is described. The corresponding mono- and dialkylated derivatives of 2-benzimidazolethiol were obtained generally in good to excellent yields after short reaction times. Reconstructed hydrotalcite proved to be an efficient and reusable heterogeneous base for the alkylation reactions.

Supporting Information

 
  • References

  • 1 Ebitani K, Motokura K, Mori K, Mizugaki T, Kaneda K. J. Org. Chem. 2006; 71: 5440
  • 2 Xu C, Gao Y, Liu X, Xin R, Wang Z. RSC Adv. 2013; 3: 793
  • 3 Álvarez MG, Chimentão RJ, Figueras F, Medina F. Appl. Clay Sci. 2012; 58: 16
  • 4 Corma A, Hamid SB. A, Iborra S, Velty A. J. Catal. 2005; 234: 340
  • 5 Bergadà O, Vicente I, Salagre P, Cesteros Y, Medina F, Sueiras JE. Microporous Mesoporous Mater. 2007; 101: 363
  • 6 Angelescu E, Pavel OD, Bîrjega R, Florea M, Zăvoianu R. Appl. Catal., A 2008; 341: 50
  • 7 Mokhtar M, Inayat A, Ofili J, Schwieger W. Appl. Clay Sci. 2010; 50: 176
  • 8 Sharma SK, Parikh PA, Jasra RV. Appl. Catal., A 2010; 386: 34
  • 9 Vaz PD, Nunes CD. New J. Chem. 2010; 34: 541
    • 10a Anuar MR, Abdullah AZ, Othman MR. Catal. Commun. 2013; 32: 67
    • 10b Zeng H.-y, Feng Z, Deng X, Li Y.-q. Fuel 2008; 87: 3071
  • 11 Yu S, Kim E, Park S, Song IK, Jung JC. Catal. Commun. 2012; 29: 63
  • 12 Cardenas J, Morales-Serna JA, Sanchez E, Gavino R, Lomas L, Guerra N, Negrón G. ARKIVOC 2005; (vi): 428
  • 13 Negrón G, Guerra N, Lomas L, Gavino R, Cardenas J. ARKIVOC 2003; (xi): 179
  • 14 Guerra-Navarro NA, Palacios-Grijalva LN, Angeles-Beltrán D, Negrón-Silva GE, Lomas-Romero L, González-Zamora E, Gavino-Ramírez R, Navarrete-Bolaños J. Molecules 2011; 16: 6561
    • 15a Narasimhan B, Sharma D, Kumar P. Med. Chem. Res. 2012; 21: 269
    • 15b Bansal Y, Silakari O. Bioorg. Med. Chem. 2012; 20: 6208
    • 15c Chawla A, Kaur R, Goyal A. J. Chem. Pharm. Res. 2011; 3: 925
    • 16a Espinoza A, Negrón G, Palomar-Pardavé M, Romero-Romo MA, Rodríguez-Torres I, Herrera-Hernández H. ECS Trans. 2009; 20: 543
    • 16b Morales-Gil P, Negrón-Silva G, Romero-Romo M, Ángeles-Chávez C, Palomar-Pardavé M. Electrochim. Acta 2004; 49: 4733
  • 17 Cruz-Gonzalez DY, Negrón-Silva G, Angeles-Beltrán D, Palomar-Pardavé M, Romero-Romo M, Uruchurtu-Chavarín J. ECS Trans. 2011; 36: 197
  • 18 Van Allan JA, Deacon BD. Org. Synth., Coll. Vol. IV 1963; 569
    • 19a Kappe CO, Stadler A. Microwaves in Organic and Medicinal Chemistry . Wiley-VCH; Weinheim: 2005
    • 19b Loupy A. Microwaves in Organic Synthesis . Wiley-VCH; Weinheim: 2002
    • 19c Hayes BL. Microwave Synthesis: Chemistry at the Speed of Light. CEM; Matthews NC: 2002
    • 20a Boraei AA. A, Ahmed IT. J. Chem. Eng. Data 1996; 41: 787
    • 20b Catalán J, Claramunt RM, Elguero J, Laynez J, Menéndez M, Anvia F, Quian JH, Taagepera M, Taft RW. J. Am. Chem. Soc. 1988; 110: 4105
    • 20c Bordwell FG. Acc. Chem. Res. 1988; 21: 456
  • 21 Guravaiah N, Rajeswar Rao V. Synth. Commun. 2010; 40: 808
  • 22 Sekar R, Srinivasan M, Marcelis AT. M, Sambandam A. Tetrahedron Lett. 2011; 52: 3347
  • 23 Yaroshenko TI, Nakhmanovich AS, Larina LI, Elokhina VN, Amosova SV. Chem. Heterocycl. Compd. (Engl. Transl.) 2008; 44: 1129
  • 24 Suri PO, Khajuria RK, Saxena DB, Rawat NS, Atal CK. J. Heterocycl. Chem. 1983; 20: 813
  • 25 Klimešová V, Kočí J, Pour M, Stachel J, Waisser K, Kaustová J. Eur. J. Med. Chem. 2002; 37: 409
  • 26 Graber DR, Morge RA, Sih JC. J. Org. Chem. 1987; 52: 4620
  • 27 Lee TR, Kim K. J. Heterocycl. Chem. 1989; 26: 747