TRIMETHYL PHOSPHITE MEDIATED SIMPLE SYNTHESIS OF COUMARINS AND AZACOUMARINS THROUGH THE REACTION OF PHENOLS OR HYDROXYPYRIDINES AND DIMETHYL ACETYLENEDICARBOXYLATE (DMAD) OR DIETHYL ACETYLENEDICARBOXYLATE (DEAD)

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MORADI SHAHRAM; AZARAKHSHI F.; MASOUMI SHAHI A.

مرکز اطلاعات علمی Scientific Information Database (SID) - Trusted Source for Research and Academic Resources

Journal Paper

Paper Information

Journal: Iranian Journal of Chemistry and Chemical Engineering Year:2008 | Volume:27 | Issue:4 Page(s): 35-39

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Title

TRIMETHYL PHOSPHITE MEDIATED SIMPLE SYNTHESIS OF COUMARINS AND AZACOUMARINS THROUGH THE REACTION OF PHENOLS OR HYDROXYPYRIDINES AND DIMETHYL ACETYLENEDICARBOXYLATE (DMAD) OR DIETHYL ACETYLENEDICARBOXYLATE (DEAD)

Author(s)

MORADI SHAHRAM | AZARAKHSHI F. | MASOUMI SHAHI A. | Issue Writer Certificate

Keywords

2-OXO-2H-CHROMENES

AZACOUMARINS

ACETYLENICESTER

AROMATIC SUBSTITUTION

TRIMETHYL PHOSPHATE

Abstract

Protonation of the reactive intermediate produced in the reaction between trimethyl phosphite and dimethyl acetylenedicarboxylate or diethyl acetylenedicarboxylate by resorcinol, 5- methylresorcinol, 2,5-dihydroxyacetophenone, 4-chloro-2-methylphenol, 4-chloro-3,5-dimethylphenol, 4-hydroxypyridine, 2-hydroxypyridine, 3-hydroxypyridine, or 8-hydroxyquinoline leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of the OH-acid to produce highly functionalized 2-oxo-2H-chromene or AZACOUMARINS in good yields.

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APA: Copy

MORADI, SHAHRAM, AZARAKHSHI, F., & MASOUMI SHAHI, A.. (2008). TRIMETHYL PHOSPHITE MEDIATED SIMPLE SYNTHESIS OF COUMARINS AND AZACOUMARINS THROUGH THE REACTION OF PHENOLS OR HYDROXYPYRIDINES AND DIMETHYL ACETYLENEDICARBOXYLATE (DMAD) OR DIETHYL ACETYLENEDICARBOXYLATE (DEAD). IRANIAN JOURNAL OF CHEMISTRY AND CHEMICAL ENGINEERING (IJCCE), 27(4), 35-39. SID. https://sid.ir/paper/549124/en

Vancouver: Copy

MORADI SHAHRAM, AZARAKHSHI F., MASOUMI SHAHI A.. TRIMETHYL PHOSPHITE MEDIATED SIMPLE SYNTHESIS OF COUMARINS AND AZACOUMARINS THROUGH THE REACTION OF PHENOLS OR HYDROXYPYRIDINES AND DIMETHYL ACETYLENEDICARBOXYLATE (DMAD) OR DIETHYL ACETYLENEDICARBOXYLATE (DEAD). IRANIAN JOURNAL OF CHEMISTRY AND CHEMICAL ENGINEERING (IJCCE)[Internet]. 2008;27(4):35-39. Available from: https://sid.ir/paper/549124/en

IEEE: Copy

SHAHRAM MORADI, F. AZARAKHSHI, and A. MASOUMI SHAHI, “TRIMETHYL PHOSPHITE MEDIATED SIMPLE SYNTHESIS OF COUMARINS AND AZACOUMARINS THROUGH THE REACTION OF PHENOLS OR HYDROXYPYRIDINES AND DIMETHYL ACETYLENEDICARBOXYLATE (DMAD) OR DIETHYL ACETYLENEDICARBOXYLATE (DEAD),” IRANIAN JOURNAL OF CHEMISTRY AND CHEMICAL ENGINEERING (IJCCE), vol. 27, no. 4, pp. 35–39, 2008, [Online]. Available: https://sid.ir/paper/549124/en

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