The clean and mild synthesis, crystal structure, and intra-molecular hydrogen bond study of substituted new 4,8-dihydropyrano[3,2-b]-pyrans containing chlorokojic acid moiety

Aghbash K. O., Pesyan N. N., Marandi G., DEGE N., ŞAHİN E.

RESEARCH ON CHEMICAL INTERMEDIATES, vol.45, no.9, pp.4543-4554, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 45 Issue: 9
  • Publication Date: 2019
  • Doi Number: 10.1007/s11164-019-03848-7
  • Journal Name: RESEARCH ON CHEMICAL INTERMEDIATES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Page Numbers: pp.4543-4554
  • Keywords: Chlorokojic acid, Isocyanides, Acetylene esters, Nucleophilic addition, 4H-Pyran, 4, 8-Dihydropyrano[3, 2-b]-pyran, Intramolecular H bond, Inversion dimers, DERIVATIVES, ANTICONVULSANT, ISOCYANIDES
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

A safe, green and convenient process was developed for the synthesis of a novel group of 4,8-dihydropyrano[3,2-b]-pyrans by dialkyl acetylenedicarboxylates and alkyl isocyanides being trapped by chlorokojic acid in good to excellent yields at ambient temperature. Characterization of all structures was carried out by FT-IR and H-1 and C-13 NMR spectrometers, and two compounds were analyzed using X-ray diffraction technique. Crystal structures showed an intramolecular hydrogen bond and stacking of the dimeric (RS) molecules with the unit cell along the a-axis.