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 Karami; Behrouz Notash

doi:10.1055/s-0040-1707132

Synthesis, Table of Contents

Synthesis 2020; 52(21): 3243-3252
DOI: 10.1055/s-0040-1707132

special topic

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

Morteza Shiri ∗

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran Email: mshiri@alzahra.ac.ir

,

Zahra Gholami-Koupaei

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran Email: mshiri@alzahra.ac.ir

,

Farzaneh Bandehali-Naeini

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran Email: mshiri@alzahra.ac.ir

,

Maryam-Sadat Tonekaboni

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran Email: mshiri@alzahra.ac.ir

,

Saeedeh Soheil-Moghaddam

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran Email: mshiri@alzahra.ac.ir

,

Delaram Ebrahimi

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran Email: mshiri@alzahra.ac.ir

,

Sima Karami

^aDepartment of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran 1993893973, Iran Email: mshiri@alzahra.ac.ir

,

Behrouz Notash

^bDepartment of Inorganic Chemistry and Catalysis, Shahid Beheshti University, General Campus, Evin, Tehran 1983963113, Iran

› Author Affiliations

Abstract

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Published as part of the Special Topic Recent Advances in Amide Bond Formation

Abstract

A post-Passerini condensation transformation can be employed in the synthesis of three types of amides: α-hydroxy, α-oxy, and α-oxo amides. K₂CO₃ efficiently promotes the solvolysis of α-acetoxy amides to form α-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-3-yl]acetamides with I₂ in basic media produces pyrrolo[2,3-b]quinoline-2,3-diones. This cyclization involves intramolecular cyclization, dealkynylative aromatization, and oxidation of the secondary alcohol.

Key words

Passerini adduct - post-condensation transformation - cascade reaction - iodine - cyclization - deacetylation - dealkynylation

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References

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