One‐pot synthesis of 3‐(sulfonyl)‐5,6,7,8‐tetrahydro‐4H‐pyrano[3,2‐c]pyridines through a cascade Michael/cyclization reaction

Abstract

In this paper, a straightforward and valid three-component Michael/cyclization reaction of (E)-1-methyl-3-(arylidene)piperidin-4-ones, 2-(sulfonyl)acetonitriles, and aromatic aldehydes was explored for the preparation of potentially biologically active 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridines under mild reaction conditions. More diverse 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine derivatives were constructed in satisfactory yields (up to 97%). The chemical structure of newly synthesized 3-(sulfonyl)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c] pyridines were identified with 1 H-NMR, 13 C-NMR, and mass spectrometry analysis. The recommendable method features a simple and direct workup, easy access to initial materials, high atom utilization efficiency, high final product yields, and a wide range of substrate adaptability. K E Y W O R D S cyclization, hexahydropyridine, Michael addition, multicomponent reactions, sulfonyl-4H-pyrano [3,2-c]pyridine

Convenient synthesis of 8‐aryl‐6‐aryl‐1,2,3,4‐tetrahydroisoquinoline‐5,7‐dicarbonitriles via a cascade Michael/cyclization reaction

“…However, no researcher has explored the reaction when adding these three raw materials at the same time. It is worth noting that the utilization of "multicomponent reactions (MCRs)" strategy shows a number of obvious advantages and gets a growing number of successful applications in many aspects [37][38][39] . In contrast to multistep reactions, MCRs convert multiple molecules straightly to the desired products in only one step reaction with higher atom economy, simpler operation process, more complex and diverse molecular structures.…”