Published June 8, 2020 | Version v1
Journal article Open

Highly Selective Synthesis of α-Hydroxy, α-Oxy, and α-Oxo Amides by a Post-Passerini Condensation Transformation

Authors/Creators

  • 1. Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran, Iran.

Description

A post-Passerini condensation transformation can be employed in the synthesis of three types of amides: a-hydroxy, a-oxy, and a-oxo amides. K2CO3 efficiently promotes the solvolysis of a-acetoxy amides to form a-hydroxy amides in methanol. 2-Acetoxy-2-(2-alkynylquinolin-3-yl)acetamides in basic methanol are cyclized to 1,3-dihydrofuro[3,4-b]quinoline-1-carboxamides via deacetylation and 5-exo-dig cyclization. Treatment of 2-hydroxy-2-[2-(phenylethynyl)quinolin-3yl]acetamides with I2 in basic media produces pyrrolo[2,3-b]quinoline2,3-diones. This cyclization involves intramolecular cyclization, dealkynylative aromatization, and oxidation of the secondary alcohol.

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