Novel domino procedures for the synthesis of chromene derivatives and their isomerization

Afsaneh Zonouzi; Zakieh Izakian; Seik Weng Ng

doi:10.1007/s11030-016-9664-0

Novel domino procedures for the synthesis of chromene derivatives and their isomerization

Mol Divers. 2016 Aug;20(3):627-38. doi: 10.1007/s11030-016-9664-0. Epub 2016 Mar 22.

Authors

Afsaneh Zonouzi^{1

2}, Zakieh Izakian^{3

4}, Seik Weng Ng^{5

6}

Affiliations

¹ School of Chemistry, University College of Science, University of Tehran, Tehran, Iran. zonouzi70@gmail.com.
² Pharmaceutical and Cosmetic Research Center (PCRC), University of Tehran Research Institute, Tehran, Iran. zonouzi70@gmail.com.
³ School of Chemistry, University College of Science, University of Tehran, Tehran, Iran.
⁴ Pharmaceutical and Cosmetic Research Center (PCRC), University of Tehran Research Institute, Tehran, Iran.
⁵ Department of Chemistry, University of Malaya, 50603, Kuala Lumpour, Malaysia.
⁶ Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia.

PMID: 27003393
DOI: 10.1007/s11030-016-9664-0

Abstract

Novel tricyclic keto diesters have been synthesized by a one-pot three-component procedure via DABCO-catalyzed domino Knoevenagel-Michael addition reactions. Also, an efficient four-component reaction for the synthesis of another new group of tricyclic keto diesters has been developed via domino Knoevenagel-intramolecular oxo-Diels-Alder reactions. A selective thermal isomerization of the synthesized chromenes to fumarates is also described. X-ray analyses confirm unambiguously the structures of the products.

Keywords: Chromene; DABCO; Domino reaction; Iminolactone; Isomerization; MCRs; Michael addition; Oxo-Diels–Alder.

MeSH terms

Benzopyrans / chemical synthesis*
Benzopyrans / chemistry
Catalysis
Cyclization
Cycloaddition Reaction
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry
Molecular Structure
Stereoisomerism

Substances

Benzopyrans
Heterocyclic Compounds