Abstract
We report an unprecedented multicomponent reaction of acetoacetanilide with malononitrile leading to a structurally novel bicyclic product (9) in a high yield. The structure has been confirmed by X-ray crystallography and comparative Hirshfeld surface analysis of 5-cyano-2-hydroxy-2-methyl-N-phenyl-4-(yridine-4-yl)-6-(thiophen-2-yl)-3,4-dihydro-2H-pyran-3-carboxamide 2, 5-cyano-2-hydroxy-2-methyl-6-oxo-N-phenyl-4-(thiophen-2-yl)piperidine-3-carboxamide 4 and 2-(8-amino-7,8a-dicyano-1-imino-4a-methyl-3-oxo-2-phenyl-1,3,4,4a,5,8a-hexahydroisoquinolin-6(2H)-ylidene)-N-phenylacetamide 9.
Highlights
Pyridone, piperidine, pyran, and isoquinoline moieties are functional components of various natural products [1,2,3], pharmaceuticals [4,5,6], and biologically active compounds [7,8,9].Two-component [10] and multicomponent [11,12,13] tandem transformations leading to these heterocyclic systems are attractive from the point of view of diversity-oriented synthesis because of their modularity and rapid buildup of molecular complexity
Previous works on acetoacetanilide 1 with various ylidenes [14,15,16,17]
To explain its formation, we propose the reaction acetoacetanilide and andtwo twomolecules molecules of malononitrile
Summary
Piperidine, pyran, and isoquinoline moieties are functional components of various natural products [1,2,3], pharmaceuticals [4,5,6], and biologically active compounds [7,8,9]. Two-component [10] and multicomponent [11,12,13] tandem transformations leading to these heterocyclic systems are attractive from the point of view of diversity-oriented synthesis because of their modularity and rapid buildup of molecular complexity. We disclose a high-yielding synthesis of a structurally novel bicyclic heterocycle from two simple starting materials
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
