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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 14
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Original Articles

Convenient Synthesis of 2-Aminothiophene Derivatives by Acceleration of Gewald Reaction Under Ultrasonic Aqueous Conditions

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Pages 2067-2074 | Received 18 Apr 2009, Published online: 17 Jun 2010

REFERENCES

  • Mason , T. J. ; Lorimer , J. P. Applied Sonochemistry: Uses of Power Ultrasound in Chemistry and Processing ; Wiley-VCH : Weinheim , 2002 .
  • Cravotto , G. ; Cintas , P. Power ultrasound in organic synthesis: Moving cavitational chemistry from academia to innovative and large-scale applications . Chem. Soc. Rev. 2006 , 35 , 180 – 196 .
  • (a) Cravotto , G. ; Cintas , P. Forcing and controlling chemical reactions with ultrasound . Angew. Chem. Int. Ed. 2007 , 46 , 5476 – 5478 ; (b) Zhang , Z. H. ; Zha , Z. G. ; Gan , C. S. ; Pan , C. F. ; Zhou , Y. Q. ; Wang , Z. Y. ; Zhou , M. M. Catalysis and regioselectivity of the aqueous Heck reaction by Pd(0) nanoparticles under ultrasonic irradiation . J. Org. Chem. 2006 , 71 , 4339 – 4342 .
  • (a) Abaee , M. S. ; Hamidi , V. ; Mojtahedi , M. M. Ultrasound-promoted aminolysis of epoxides in aqueous media: A rapid procedure with no pH adjustment for additive-free synthesis of β-aminoalcohols . Ultrason. Sonochem. 2007 , 15 , 823 – 827 ; (b) Gholap , A. R. ; Venkatesan , K. ; Daniel , T. ; Lahoti , R. J. ; Srinivasan , K. V. Ultrasound-promoted acetylation of alcohols in room-temperature ionic liquid under ambient conditions . Green Chem. 2003 , 5 , 693 – 696 ; (c) Mojtahedi , M. M. ; Saidi , M. R. ; Shirzi , J. S. ; Bolourtchian , M. Ultrasound-accelerated reductive coupling of imine or iminium ion generated in 5 M lithium perchlorate solution by lithium metal . Synth. Commun. 2001 , 31 , 3587 – 3592 ; (d) Mojtahedi , M. M. ; Javadpour , M. ; Abaee , M. S. Convenient ultrasound-mediated synthesis of substituted pyrazolones under solvent-free conditions . Ultrason. Sonochem. 2007 , 15 , 828 – 832 .
  • (a) Zhu , J. ; Bienayme , H. Multicomponent Reactions ; Wiley-VCH : Weinheim , 2005 ; (b) Domling , A. ; Ugi , I. Multicomponent reactions with isocyanides. Angew. Chem. Int. Ed. 2000, 39, 3168–3210 .
  • (a) Kappe , C. O. Recent advances in the Biginelli dihydropyrimidine synthesis: New tricks from an old dog . Acc. Chem. Res. 2000 , 33 , 879 – 888 ; (b) Armstrong , R. W. ; Combs , A. P. ; Tempest , P. A. ; Brown , S. D. ; Keating , T. A. Multiple-component condensation strategies for combinatorial library synthesis . Acc. Chem. Res. 1996 , 29 , 123 – 131 .
  • (a) Gewald , K. Methods for the synthesis of 2-aminothiophenes and their reactions . Chem. Heterocycl. Comp. 1976 , 12 , 1077 – 1090 ; (b) Sabnis , R. W. The Gewald synthesis . Sulfur Reports 1994 , 16 , 1 – 17 .
  • (a) Sabins , R. W. ; Rangnekar , D. W. ; Sonawane , N. D. 2-Aminothiophenes by the Gewald reaction. J. Heterocycl. Chem. 1999, 36, 333–345; (b) Blackburn , T. P. ; Davies , D. T. ; Forbes , I. T. ; Hayward , C. J. ; Johnson , C. N. ; Martin , R. T. ; Piper , D. C. ; Thomas , D. R. ; Thompson , M. ; Upton , N. ; Ward , R. W. Isosteric replacement of the indole nucleus by benzothiophene in a series of pyrido[2,3-b]indoles with potential anxiolytic activity. Bioorg. Med. Chem. Lett. 1995, 5, 2589–2592; (c) Andersen , H. S. ; Olsen , O. H. ; Iversen , L. F. ; Sørensen , A. L. P. ; Mortensen , S. B. ; Christensen , M. S. ; Branner , S. ; Hansen , T. K. ; Lau , J. F. ; Jeppesen , L. ; Moran , E. J. ; Su , J. ; Bakir , F. ; Judge , L. ; Shahbaz , M. ; Collins , T. ; Vo , T. ; Newman , M. J. ; Ripka , W. C. ; Møller , N. P. H. Discovery and SAR of a novel selective and orally bioavailable nonpeptide classical competitive inhibitor class of protein-tyrosine phosphatase 1B. J. Med. Chem. 2002, 45, 4443–4459.
  • Hagen , H. ; Nilz , G. ; Walter , H. ; Landes , A. Herbicidal agents containing substituted 2-aminothiophene . German Patent 4039734, 1992 .
  • Fu , T. L. ; Wang , I. J. Synthesis and characterization of some novel polyfunctionally substituted indeno[2,1-b]thiophene compounds derived from indanones . Dyes Pigments 2008 , 76 , 590 – 595 .
  • Koike , K. ; Jia , Z. H. ; Nikaido , T. ; Liu , Y. ; Zhao , Y. Y. ; Guo , D. Echinothiophene, a novel benzothiophene glycoside from the roots of Echinops grijissii . Org. Lett. 1999 , 1 , 197 – 198 .
  • Arhin , F. ; Belanger , O. ; Ciblat , S. ; Dehbi , M. ; Delorme , D. ; Dietrich , E. ; Dixit , D. ; Lafontaine , Y. ; Lehoux , D. ; Liu , J. ; McKay , G. A. ; Moeck , G. ; Reddy , R. ; Rose , Y. ; Srikumar , R. ; Tanaka , K. S. E. ; Williams , D. M. ; Gros , P. ; Pelletier , J. ; Parr , T. R. ; Far , A. R. A new class of small molecule RNA polymerase inhibitors with activity against Rifampicin-resistant Staphylococcus aureus . Bioorg. Med. Chem. 2006 , 14 , 5812 – 5832 .
  • Gewald , K. Zur reaktion von α-oxo-mercaptanen mit nitrilen . Angew. Chem. 1961 , 73 , 114 – 114 .
  • (a) Tormyshev , V. M. ; Trukhin , D. V. ; Rogozhnikova , O. Y. ; Mikhalina , T. V. ; Troitskaya , T. I. ; Flinn , A. Aryl alkyl ketones in a one-pot Gewald synthesis of 2-aminothiophenes . Synlett 2006 , 2559 – 2564 ; (b) Gütschow , M. ; Schroter , H. ; Kuhnle , G. ; Eger , K. Synthesis of 4-isobutyl substituted thiophenes by Gewald reaction . Monatsh. Chem. 1996 , 127 , 297 – 303 .
  • (a) Hu , Y. ; Wei , P. ; Huang , H. ; Han , S. Q. ; Ouyang , P. K. Synthesis of 2-aminothiophenes on ionic liquid phase support using the Gewald reaction . Synth. Commun. 2006 , 36 , 1543 – 1548 ; (b) Buchstaller , H. P. ; Siebert , C. D. ; Lyssy , R. H. ; Frank , I. ; Duran , A. ; Gottschlich , R. ; Noe , C. R. Synthesis of novel 2-aminothiophene-3-carboxylates by variations of the Gewald reaction . Monatsh. Chem. 2001 , 132 , 279 – 293 ; (c) Hu , Y. ; Chen , Z. C. ; Le , Z. G. ; Zheng , Q. G. Organic reactions in ionic liquids: Gewald synthesis of 2-aminothiophenes catalyzed by ethylenediammonium diacetate . Synth. Commun. 2004 , 34 , 3801 – 3806 ; (d) Feroci , M. ; Chiarotto , I. ; Rossi , L. ; Inesi , A. Activation of elemental sulfur by electrogenerated cyanomethyl anion: Synthesis of substituted 2-aminothiophenes by the Gewald reaction . Adv. Synth. Catal. 2008 , 350 , 2740 – 2746 .
  • (a) Hesse , S. ; Perspicace , E. ; Kirsch , G. Microwave-assisted synthesis of 2-aminothiophene-3-carboxylic acid derivatives, 3H-thieno[2,3-d]pyrimidin-4-one and 4-chlorothieno[2,3-d]pyrimidine. Tetrahedron Lett. 2007, 48, 5261–5264; (b) Hoener , A. P. F. ; Henkel , B. ; Gauvin , J. C. Novel one-pot microwave-assisted Gewald synthesis of 2-acyl amino thiophenes on solid support. Synlett 2003, 63–66; (c) Hesse , S. ; Perspicace , E. ; Kirsch , G. Microwave-assisted synthesis of 2-aminothiophene-3-carboxylic acid derivatives, 3H-thieno[2,3-d]pyrimidin-4-one and 4-chlorothieno[2,3-d]pyrimidine. Tetrahedron Lett. 2007, 48, 5261–5264; (d) Huang , W. ; Li , J. ; Tang , J. ; Liu , H. ; Shen , J. H. ; Jiang , H. L. Microwave-assisted synthesis of 2-amino-thiophene-3-carboxylic derivatives under solvent-free conditions. Synth. Commun. 2005, 35, 1351–1357; (e) Zhang , H. Q. ; Yang , G. C. ; Chen , J. N. ; Chen , Z. X. Synthesis of thiophene derivatives on soluble polymer-support using Gewald reaction. Synthesis 2004, 3055–3059.
  • (a) Wang , M. L. ; Rajendran , V. Kinetics for dichlorocyclopropanation of 1,7-octadiene under the influence of ultrasound assisted phase-transfer catalysis conditions . J. Mol. Catal. A: Chem. 2007 , 273 , 5 – 13 ; (b) Entezari , M. H. ; Heshmati , A. ; Yazdi , A. S. A combination of ultrasound and inorganic catalyst: Removal of 2-chlorophenol from aqueous solution . Ultrason. Sonochem. 2005 , 12 , 137 – 141 .
  • Barnes , D. M. ; Haight , A. R. ; Hameury , T. ; McLaughlin , M. A. ; Mei , J. Z. ; Tedrow , J. S. ; Toma , J. D. R. New conditions for the synthesis of thiophenes via the Knoevenagel/Gewald reaction sequence: Application to the synthesis of a multitargeted kinase inhibitor . Tetrahedron 2006 , 62 , 11311 – 11319 .

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