Research Article

Synthesis and Characterization of Novel 2,4-Diaryloctahydro-2H-Chromene Derivatives with Four Stereocenters

Volume: 44 Number: 4 December 28, 2023
EN

Synthesis and Characterization of Novel 2,4-Diaryloctahydro-2H-Chromene Derivatives with Four Stereocenters

Abstract

Chromene derivatives are among the natural compounds and they can also be easily obtained synthetically. They are one of the most commonly used skeletons in heterocyclic chemistry. Chromene derivatives are used in the cosmetic and pigment industries as well as having a wide spectrum of biological activity. Synthesis of chromene derivatives and their application areas is a current topic. In this study, it is aimed to synthesis and characterization of new chromene derivatives by catalysis of molecular iodine starting from 1,5-diol derivatives with chiral centers. In this context, 8 new 2,4-diaryloctahydro-2H-chromene derivatives were synthesized in high yields and their structure determinations were made by spectroscopic methods (1H-NMR, 13C-NMR, 2D-NMR, GCMS and FTIR) and their stereochemistry was determined.

Keywords

Supporting Institution

Gaziosmanpaşa Üniversitesi

Project Number

BAP-201194

References

  1. [1] Eicher T., Hauptmann S. & Speichcr, A., The Chemistry of Heterocycles: Structure, Reactions, Synthesis and Applications.2nd ed. Weinheim (2004) 341-345.
  2. [2] Wen Z., Yang K.-C., Deng J.-F. & Chen L., Advancements in the preparation of 4H-chromenes: an overview, Advanced Synthesis & Catalysis, 365 (2023) 1290-1331.
  3. [3] Singh M. M., Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders, Medicinal Research Reviews, 21 (2001) 302-347.
  4. [4] Hilas O. & Ezzo D., Nebivolol (bystolic), a novel beta blocker for hypertension, Pharmacy and Therapeutics, 34(4) (2009) 188-192.
  5. [5] Mamaghani M., Nia H. R., Tavakoli F. & Jahanshahi P., Recent Advances in the MCRs Synthesis of Chromenes: A Review, Current Organic Chemistry, 22(17) (2018) 1704 - 1769.
  6. [6] Raj V. & Lee J., 2H/4H-Chromenes-a versatile biologically attractive scaffold, Frontiers in Chemistry, 8(623) (2020) 1-23.
  7. [7] Bianchi G. & Tava, A., Synthesis of (2R)-(+)-2,3-Dihydro-2,6-dimethyl-4H-pyran-4-one, a Homologue of Pheromones of a Species in the Hepialidae Family, Agricultural and Biological Chemistry, 51 (1987) 2001-2002.
  8. [8] Tangmouo J. G., Meli A. L., Komguem J., Kuete V., Ngounou F. N., Lontsi D., Beng V. P., Houdhary M. L. & Sondengam B. L., Crassiflorone, a new naphthoquinone from Diospyros crassiflora (Hien), Tetrahedron Letter, 47 (2006) 3067-3070.

Details

Primary Language

English

Subjects

Organic Chemical Synthesis

Journal Section

Research Article

Publication Date

December 28, 2023

Submission Date

August 11, 2023

Acceptance Date

November 13, 2023

Published in Issue

Year 1970 Volume: 44 Number: 4

APA
Gezegen, H. (2023). Synthesis and Characterization of Novel 2,4-Diaryloctahydro-2H-Chromene Derivatives with Four Stereocenters. Cumhuriyet Science Journal, 44(4), 678-686. https://doi.org/10.17776/csj.1341173

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