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Multicomponent synthesis of pyridines via diamine functionalized mesoporous ZrO2 domino intramolecular tandem Michael type addition†
Ramakanth Pagadala,Devendar Reddy Kommidi,Surjyakanta Rana,Suresh Maddila,Brenda Moodley,N. A. Koorbanally,Sreekantha B. Jonnalagadda
RSC Advances Pub Date : 12/03/2014 00:00:00 , DOI:10.1039/C4RA13552K
Abstract

A new and straightforward synthetic method was developed for the facile synthesis of heterocycle-fused pyridine derivatives in aqueous media from Knoevenagel condensation between an aromatic aldehyde and an active methylene compound. This was followed by Michael type addition of a ketone to the activated double bond of the arylidene via intramolecular cyclization in the presence of diamine functionalized [N-(2 amino ethyl)-3-amino propyl trimethoxy silane (AAPTMS)] mesoporous ZrO2 (AAPTMS/m-ZrO2) to synthesize fused pyridines in high yield. This one-pot conversion, which involves multiple steps and requires no toxic/organic solvents, produced new C–C and C–heteroatom bonds with all reactants efficiently utilized.

Graphical abstract: Multicomponent synthesis of pyridines via diamine functionalized mesoporous ZrO2 domino intramolecular tandem Michael type addition
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