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One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides.

ABSTRACT: A novel one-pot tandem process involving Knoevenagel condensation, Michael addition, selective amidation, and Paal-Knorr cyclization to diverse functionalized 3-hydroxy-2-furanyl-acrylamides from simple 2-oxoaldehydes and aroylacetonitriles was presented. Attempts were also made to expand the scope of the reaction to different 2-heteroarylfurans. The packing diagram of the molecules viewed down along the α-axis of the unit cell showed a characteristic intramolecular classical O-H···O hydrogen bond between hydroxyl and carbonyl O atoms leading to self-associated (Z)-2-furanyl-acrylamides.

SUBMITTER: Mupparapu N

PROVIDER: S-EPMC6641926 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides.

Mupparapu Nagaraju N Khan Shahnawaz S Bandhoria Pankaj P Athimoolam Shunmuganarayanan S Ahmed Qazi Naveed QN

ACS omega 20180521 5

A novel one-pot tandem process involving Knoevenagel condensation, Michael addition, selective amidation, and Paal-Knorr cyclization to diverse functionalized 3-hydroxy-2-furanyl-acrylamides from simple 2-oxoaldehydes and aroylacetonitriles was presented. Attempts were also made to expand the scope of the reaction to different 2-heteroarylfurans. The packing diagram of the molecules viewed down along the α-axis of the unit cell showed a characteristic intramolecular classical O-H···O hydrogen bo ...[more]

PMID: 31458749

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