Eco-friendly methodology to prepare N-heterocycles related to dihydropyridines: microwave-assisted synthesis of alkyl 4-arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate and 4-arylsubstituted-4,7-dihydrofuro[3,4-b]pyridine-2,5(1H,3H)-dione

Molecules. 2011 Nov 21;16(11):9620-35. doi: 10.3390/molecules16119620.

Abstract

Here we describe the efficient synthesis of alkyl 4-arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylates and 4-arylsubstituted-4,7-dihydro-furo[3,4-b]pyridine-2,5(1H,3H)-diones via microwave-accelerated reaction of alkyl 4-arylsubstituted-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylates with the appropriate reagents. This eco-friendly approach to these valuable dihydropyridine derivatives does not involve the harsh or highly contaminating conditions common in classical heating and offers a reduction or even elimination of solvent use and recovery, simplification of the work-up procedures, facility of scale up, and low energy consumption, in addition to moderate to higher yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Dihydropyridines / chemical synthesis*
  • Dihydropyridines / chemistry
  • Drug Discovery
  • Green Chemistry Technology / methods*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Microwaves*
  • Molecular Structure
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry

Substances

  • Carboxylic Acids
  • Dihydropyridines
  • Heterocyclic Compounds
  • Pyridines