TY - JOUR ID - 6936 TI - Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD) JO - Iranian Journal of Chemistry and Chemical Engineering JA - IJCCE LA - en SN - 1021-9986 AU - Moradi, Shahram AU - Azarakhshi, Fatemeh AU - Masoumi Shahi, Akbar AD - Faculty of Chemistry, Islamic Azad University, Tehran North Branch, Tehran, I.R. IRAN AD - Department of Chemistry, Islamic Azad University, Arak Branch, Arak, I.R. IRAN Y1 - 2008 PY - 2008 VL - 27 IS - 4 SP - 35 EP - 39 KW - 2-Oxo-2H-chromenes KW - Azacoumarins KW - Acetylenicester KW - Aromatic substitution KW - Trimethyl phosphate DO - 10.30492/ijcce.2008.6936 N2 - Protonation of the reactive intermediate produced in theĀ  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-dimethy-lphenol, 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. UR - https://ijcce.ac.ir/article_6936.html L1 - https://ijcce.ac.ir/article_6936_cd9036b16a77cc53767a5929b3a780b7.pdf ER -