Simple and Efficient Method for Synthesis of Novel 4-Substituted 1-Acylthiosemicarbazides via One-Pot Multicomponent Reactions

Abstract A new one-pot, multicomponent condensation reaction of aldehydes, 2-naphthol, and 1-acylthiosemicarbazides is described as an efficient method for the synthesis of novel 4-substituted 1-acylthiosemicarbazides in the presence of p-toluenesulfonic acid (p-TSA) as a catalyst under two conditions: organic solvent and solvent-free media. The present procedure offers several advantages, such as good yields, low cost, and very easy workup.

[1]  T. Müller.  Multicomponent reactions , 2011, Beilstein journal of organic chemistry.

[2]  F. Bamoharram,et al.  A Novel Multicomponent Synthesis of 4‐Arylaminoquinazolines. , 2009 .

[3]  F. Bamoharram,et al.  A novel multi-component synthesis of 4-arylaminoquinazolines , 2009 .

[4]  M. Heravi,et al.  A novel three-component reaction for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amines , 2009 .

[5]  S. D. Samant,et al.  Exploitation of the catalytic efficacy of Mg/Al hydrotalcite for the rapid synthesis of 2-aminochromene derivatives via a multicomponent strategy in the presence of microwaves , 2009 .

[6]  S. A. Raw,et al.  A one-pot process for the regioselective synthesis of 1,3,4-trisubstituted-1H-pyrazoles , 2009 .

[7]  F. Bamoharram,et al.  A direct oxidative route for the synthesis of pyrimidines using heteropolyacids , 2009 .

[8]  N. Foroughifar,et al.  A Novel Efficient Four- and Five-Component, One-Pot Synthesis of 4-Semicarbazonoalkyl-2-naphthols. , 2008 .

[9]  M. Antalík,et al.  Acridine derivatives inhibit lysozyme aggregation , 2008, European Biophysics Journal.

[10]  A. Khosropour,et al.  A Simple and Efficient Procedure for the Synthesis of Amidoalkyl Naphthols by p‐TSA in Solution or under Solvent‐Free Conditions. , 2006 .

[11]  J. Balsells,et al.  Synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles using 1,3-dibromo-5,5-dimethylhydantoin as oxidant , 2006 .

[12]  T. Argentieri,et al.  An overview of potassium channel activators for the treatment of overactive bladder: a survey of new structures 2000 – 2005 , 2006 .

[13]  A. Khosropour,et al.  A Facile, Simple and Convenient Method for the Synthesis of 14-Alkyl or Aryl-14-H-dibenzo[a,j]xanthenes Catalyzed by pTSA in Solution and Solvent-Free Conditions. , 2005 .

[14]  P. Bhuyan,et al.  Sodium Bromide Catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]pyrans via a Three-Component Cyclocondensation under Microwave Irradiation and Solvent-Free Conditions. , 2005 .

[15]  P. Bhuyan,et al.  Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions , 2004 .

[16]  A. Meetsma,et al.  A three-component reaction of phenol, aldehyde, and active methylene substrate under Lewis acid catalysis: Successful trapping of o-quinone methide to afford benzopyran systems , 2004 .

[17]  K. Zamani,et al.  Synthesis and Antimicrobial Activity of Some Pyridyl and Naphthyl Substituted 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives , 2004 .

[18]  C. Saikia,et al.  A facile synthesis of 1,7-dicarbonyl compounds via three-component Michael addition reactions , 2004 .

[19]  Limin Wang,et al.  Yb(OTf)3-Catalyzed One-Pot Synthesis of Quinazolin-4(3H)-ones from Anthranilic­ Acid, Amines and Ortho Esters (or Formic Acid) in Solvent-Free Conditions , 2003 .

[20]  A. Dömling.  Recent advances in isocyanide-based multicomponent chemistry. , 2002, Current opinion in chemical biology.

[21]  Romualdas Smicius,et al.  Synthesis of 1-(6-Methyl-2,4-Dioxo-1,2,3,4-Tetrahydro-3-Pyrimidinyl)Acetyl-4-Alkyl(Aryl)Thiosemicarbazides and their Heterocyclisation to 1,2,4-Triazoles and 1,3,4-Thiadiazoles † , 2002 .

[22]  Lutz Weber,et al.  Multi-component reactions and evolutionary chemistry. , 2002, Drug discovery today.

[23]  S. Rollas,,et al.  Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities. , 2001, Farmaco.

[24]  Aleksandra Buzarovska,et al.  Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles , 2001, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.

[25]  I. Ugi,et al.  Multicomponent Reactions with Isocyanides. , 2000, Angewandte Chemie.

[26]  L. Tietze.  Domino Reactions in Organic Synthesis. , 1996, Chemical reviews.

[27]  S. Singh,et al.  Chemistry and biological activity of thiazolidinones , 1981 .