Multistep Microwave-Assisted Solvent-Free Organic Reactions: Synthesis of 4-Oxo-tetrahydro-pyridine

Abstract Preparation and ring-closure of 2-dimethylaminomethylene-5-substituted-3-oxo-pent-4-enoic acid benzyl esters to dihydropyridine rings are efficiently and quickly carried out under solvent-free conditions in an open-vessel microwave system. The syntheses of 1,6-disubstituted-4-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid benzyl esters are reported.

[1]  A. Loupy Microwaves in organic synthesis , 2002 .

[2]  Anders Hallberg,et al.  Microwave-accelerated homogeneous catalysis in organic chemistry. , 2002, Accounts of chemical research.

[3]  Peter O. Krutzik,et al.  Increasing rates of reaction: microwave-assisted organic synthesis for combinatorial chemistry. , 2002, Journal of combinatorial chemistry.

[4]  J. Tierney,et al.  Microwave assisted organic synthesis-a review , 2001 .

[5]  A. Loupy,et al.  A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations , 2001 .

[6]  D. Comins,et al.  Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: asymmetric synthesis of 1-deoxynojirimycin , 2001 .

[7]  D. Comins,et al.  Asymmetric synthesis of (+)-deoxoprosopinine. , 2001, The Journal of organic chemistry.

[8]  M. Serio,et al.  Effect of C-ring modifications in benzo[c]quinolizin-3-ones, new selective inhibitors of human 5 alpha-reductase 1. , 2001, Bioorganic & medicinal chemistry.

[9]  E. Bandini,et al.  Synthesis of perhydroxazin-4-ones. Competitive Mukaiyama versus hetero Diels–Alder reaction in the cycloaddition of 2-aza-3-trimethylsilyloxy-1,3-butadiene and aldehydes , 2001 .

[10]  A. Mohammadi,et al.  MICROWAVE IRRADIATION PROMOTED REACTIONS OF ANTHRANILIC ACID WITH KETONES. PREPARATION OF SUBSTITUTED ACRIDINONES AND QUINOLINONES , 2001 .

[11]  A. Moreno,et al.  CYCLOADDITIONS UNDER MICROWAVE IRRADIATION CONDITIONS: METHODS AND APPLICATIONS , 2000 .

[12]  H. Sun,et al.  A simple and stereospecfic route to 2,6-disubstituted 4-hydroxypiperidines. Synthesis of dendrobate alkaloid (+)-241D and formal synthesis of (-)-indolizidine 167B. , 2000, Organic letters.

[13]  D. Comins,et al.  Asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid , 2000 .

[14]  M. Gianotti,et al.  Solvent-Free Microwave-Assisted Organic Reactions Preparation of β-Keto Esters , 2000 .

[15]  M. Serio,et al.  Synthesis of 8-chloro-benzo[c]quinolizin-3-ones as potent and selective inhibitors of human steroid 5alpha-reductase 1. , 2000, Bioorganic & medicinal chemistry letters.

[16]  D. Comins,et al.  Addition of metallo enolates to chiral 1-acylpyridinium salts: total synthesis of (+)-cannabisativine. , 2000, Organic letters.

[17]  Shenlin Huang,et al.  Total synthesis of (+)-streptazolin , 2000 .

[18]  R. Al-awar,et al.  Asymmetric Synthesis of the Lycopodium Alkaloid, Na-Acetyl-Nb-methylphlegmarine , 1999 .

[19]  A. Petit,et al.  New Solvent-Free Organic Synthesis Using Focused Microwaves , 1998 .

[20]  D. Dittmer ′No-Solvent′ Organic Synthesis , 1998 .

[21]  E. Díez-Barra,et al.  Microwave irradiation: more than just a method for accelerating reactions , 1998 .

[22]  Y. Bousquet,et al.  Preparation of enantiopure 4-oxygenated pipecolic acid derivatives , 1997 .

[23]  H. Waldmann,et al.  Construction of the tricyclic benzoquinolizine ring system by combination of a tandem Mannich-Michael reaction with a Heck reaction , 1997 .

[24]  S. Ofner,et al.  SAR of 2-benzyl-4-aminopiperidines: CGP 49823, an orally and centrally active non-peptide NK1 antagonist , 1996 .

[25]  C. R. Strauss,et al.  Developments in Microwave-Assisted Organic Chemistry , 2010 .

[26]  S. Caddick Microwave assisted organic reactions , 1995 .

[27]  G. Gaviraghi,et al.  Synthesis and antimicrobial activity of DNA-gyrase inhibiting derivatives of 4-oxo-1,4-dihydro-3-pyridinecarboxylic acid. , 1993, Il Farmaco.

[28]  R. K. Boeckman,et al.  Methodology for the synthesis of phosphorus-activated tetramic acids: applications to the synthesis of unsaturated 3-acyltetramic acids , 1982 .