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

Morteza Shiri, Zahra Gholami-Koupaei, Farzaneh Bandehali-Naeini, Maryam-Sadat Tonekaboni, Saeedeh Soheil-Moghaddam, Delaram Ebrahimi, Sima Karamia, Behrouz Notash
2021 figshare.com  
A post-Passerini condensation transformation can be employed in the synthesis of three types of amides: -hydroxy, -oxy, and -oxo amides. K2CO3 efficiently promotes the solvolysis of -acetoxy amides to form -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
more » ... ia produces pyrrolo[2,3-b]quinoline2,3-diones. This cyclization involves intramolecular cyclization, dealkynylative aromatization, and oxidation of the secondary alcohol.
doi:10.6084/m9.figshare.14119796.v1 fatcat:cztp6ppznjdvdlo2ndftptds7u