Abstract
An efficient synthesis of thiophene derivatives is described via one-pot reaction between ammonium thiocyanate, acyl chlorides, α-halocarbonyls, and enaminones under solvent-free conditions at 65 °C. The mild reaction conditions and high yields of the products exhibit the good synthetic advantage of these methods.
Similar content being viewed by others
References
Sperry Jeffrey B, Wright DL (2005) Furans, thiophenes and related heterocycles in drug discovery. Curr Opin Drug Discov Dev 8: 723–740. doi:10.1002/chin.200615242
Alhalasah W, Holze RJ (2005) Electrochemical materials science: tailoring intrinsically conducting polymers. The example: substituted thiophenes. Solid State Electrochem 9: 836–844. doi:10.1007/s10008-005-0024-8
Comel A, Sommen G, Kirsch G (2004) Thienothiophenes: synthesis and applications. Mini Rev Org Chem 1: 367–374. doi:10.1002/chin.200506247
Gronowitz S (1991) (Ed) The chemistry of heterocyclic compounds: thiophene and its derivatives, vol 44. Wiley, New York
Bertram HJ, Emberger R, Güntert M, Sommer H, Werkhoff P (1993) In: Hopp R, Mori K (eds) Recent developments in flavor and fragrance chemistry. VCH, Weinheim, pp 215–240
Roncali J (1992) Conjugated poly(thiophenes): synthesis, functionalization, and applications. Chem Rev 92: 711. doi:10.1021/cr00012a009
Skotheim TA (1986) (ed) Handbook of conductive polymers. Marcel Dekker, New York
Nalwa HS (1993) Organic materials for third-order nonlinear optics. Adv Mater 5: 341–358. doi:10.1002/chin.199335316
Tarasova OA, Klyba LV, Vvedensky VY, Nedolya NA, Trofimov BA, Brandsma L, Verkruijsse HD (1998) One-pot syntheses of 2-N-alkylamino-, 2-N-phenylamino-2-N,N-dialkylamino-and 2-N-alkyl-N-phenylaminothiophenes. Eur J Org Chem 253–256. doi:10.1002/chin.199823111.
Ong CW, Chen CM, Wang LF (1998) Convenient synthesis of 2,5-disubstituted thiophene from 1,6-dioxo-2,4-diene. Tetrahedron Lett 39: 9191–9192. doi:10.1016/S0040-4039(98)02094-2
Stephensen H, Zaragoza F (1997) Resin-bound isothiocyanates and their synthetic equivalents as intermediates for the solid-phase synthesis of substituted thiophenes. J Org Chem 62: 6096–6097. doi:10.1021/jo9709155
Marson CM, Campbell J (1997) Synthesis of polysubstituted thiophenes by a catalytic cyclisation of functionalised episulfides. Tetrahedron Lett 38: 7785–7788. doi:10.1016/S0040-4039(97)01819-4
Zhang YP, Bian M, Yao WJ et al (2009) Direct synthesis of highly substituted thiophenes through copper(I)-catalyzed tandem reactions of alkylidenethiiranes with terminal alkynes. Chem Commun 31: 4729–4731. doi:10.1039/B909284F
Gonzalez-Lopez M, Shaw JT (2009) Cyclic anhydrides in formal cycloadditions and multicomponent reactions. Chem Rev 109: 164–189. doi:10.1021/cr8002714
Wang Y, Huang J, Chai YY et al (2008) Efficient one-pot synthesis of highly substituted thiophene library from 1,3-dicarbonyl compounds. J Comb Chem 10: 511–516. doi:10.1021/cc800015b
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hossaini, Z., Rostami-Charati, F., Soltani, S. et al. Multicomponent reactions of ammonium thiocyanate, acyl chlorides, alkyl bromides, and enaminones: A facile one-pot synthesis of thiophenes. Mol Divers 15, 911–916 (2011). https://doi.org/10.1007/s11030-011-9322-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-011-9322-5