An efficient and convenient multicomponent reaction for the synthesis of 2‐methyl‐4,6‐diarylpyrimidine under solvent‐free conditions

An efficient and convenient method for the preparation of 2-methyl-4,6-diarylpyrimidine derivatives by the multicomponent reactions of aromatic aldehydes, aromatic ketones, and acetamidine hydrochloride in the presence of sodium hydroxide under solvent-free conditions was reported. This method has the advantages of excellent yields, mild reaction conditions, easy workup, and environmentally friendly procedure. J. Heterocyclic Chem., (2009).

[1]  A. Bazgir,et al.  One-pot synthesis and antibacterial activities of pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidine-dione derivatives. , 2008, Bioorganic & medicinal chemistry letters.

[2]  C. Ramalingan,et al.  Tetrachlorosilane catalyzed multicomponent one-step fusion of biopertinent pyrimidine heterocycles , 2008 .

[3]  Guolan Dou,et al.  An Efficient Synthesis of Pyrimido[4,5-b]quinoline and Indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine Derivatives via Multicomponent Reactions in Ionic Liquid. , 2008 .

[4]  J. Trujillo-Ferrara,et al.  Cyanamide: a convenient building block to synthesize 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via a multicomponent reaction , 2008 .

[5]  D. Shi,et al.  An efficient and facile procedure for the synthesis of 4,6‐diaryl‐2(1H)‐pyridones under solvent‐free conditions , 2007 .

[6]  Huanfeng Jiang,et al.  Convenient one-pot synthesis of multisubstituted tetrahydropyrimidines via catalyst-free multicomponent reactions. , 2007, Organic letters.

[7]  Bo Jiang,et al.  A Simple Synthesis of Furo[3′,4′:5,6]pyrido[2,3‐d]pyrimidine Derivatives through Multicomponent Reactions in Water , 2007 .

[8]  Zhengyin Du,et al.  New three-component cyclocondensation reaction: microwave-assisted one-pot synthesis of 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions , 2007 .

[9]  A. Basso,et al.  Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives. , 2007, The Journal of organic chemistry.

[10]  K. Scheidt,et al.  Catalytic multicomponent reactions for the synthesis of N-aryl trisubstituted pyrroles. , 2007, The Journal of organic chemistry.

[11]  D. Shi,et al.  An Efficient and Facile Synthesis of 2-Amino-4,6-diarylbenzene-1,3-dicarbonitrile and 1,2-Dihydro-2-oxo-4,6-diarylpyridine-3-carbonitrile under Solvent-free Conditions , 2006 .

[12]  B. Kaboudin,et al.  A new, efficient, and simple method for the one-pot synthesis of alpha-acetoxyphosphonates from aldehydes under solvent-free conditions. , 2006, Bioorganic & medicinal chemistry letters.

[13]  Alexander Dömling,et al.  Recent developments in isocyanide based multicomponent reactions in applied chemistry. , 2006, Chemical reviews.

[14]  R. Bon,et al.  Multicomponent synthesis of 2-imidazolines. , 2005, The Journal of organic chemistry.

[15]  A. Kiselyov.  One-pot synthesis of polysubstituted pyrimidines , 2005 .

[16]  L. Tietze,et al.  Domino reactions in the synthesis of heterocyclic natural products and analogs , 2004 .

[17]  A. Dömling,et al.  New MCRs: The first 4-component reaction leading to 2,4-disubstituted thiazoles , 2004, Molecular Diversity.

[18]  I. Ugi,et al.  The Chemistry of Isocyanides, their MultiComponent Reactions and their Libraries† , 2003, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.

[19]  K R Scott,et al.  Synthesis and anticonvulsant activity of enaminones. 4. Investigations on isoxazole derivatives. , 2002, European journal of medicinal chemistry.

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

[21]  K. Tanaka,et al.  Solvent-free organic synthesis. , 2000, Chemical reviews.

[22]  J. Stables,et al.  Enaminones-versatile therapeutic pharmacophores. Further advances. , 2000, Current medicinal chemistry.

[23]  Semenov,et al.  Controlled Arrangement of Supramolecular Metal Coordination Arrays on Surfaces. , 1999, Angewandte Chemie.

[24]  Michael Almstetter,et al.  Discovery of New Multi Component Reactions with Combinatorial Methods , 1999 .

[25]  I. Ugi,et al.  MCR 6 : CHIRAL 2,6-PIPERAZINEDIONES VIA UGI REACTIONS WITH ALPHA -AMINO ACIDS, CARBONYL COMPOUNDS, ISOCYANIDES AND ALCOHOLS , 1998 .

[26]  U. Schubert,et al.  Coordination Arrays: Tetranuclear Cobalt(II) Complexes with [2 × 2]‐Grid Structure , 1997 .

[27]  G. Dannhardt,et al.  Non‐steroidal Anti‐inflammatory Agents, Part 24[1] Pyrrolidino Enaminones as Models to Mimic Arachidonic Acid , 1997, Archiv der Pharmazie.

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

[29]  J. Rebek,et al.  Synthesis of α,α-dialkylated amino acids with adenine or thymine residues a new mild and facile hydrolysis of hydantoins , 1994 .

[30]  I. Ugi,et al.  Multicomponent reactions in organic chemistry , 1994 .

[31]  C. Heathcock.  The Enchanting Alkaloids of Yuzuriha , 1992 .

[32]  A. Keutzberger,et al.  Antimykotische Wirkstoffe, 18. Mitt. Aromatisch substituierte 2‐(4‐Toluidino)pyrimidine , 1985 .

[33]  G. N. Dorofeenko,et al.  Reaction of pyrylium salts with amidines , 1978 .