Synthesis and Transformations of Novel Acetylene Glycols Derived from N-Substituted Piperidin-4-ones

Bazhykova K.B.
February 2021 Pleiades journals

Russian Journal of Organic Chemistry
2021 #57 Issue 2 203 - 211 pp.

Abstract: With the aim to prepare asymmetric acetylenic γ-glycols, the reactions of 1-(2-ethoxyethyl)piperidin-4-one with propargyl alcohol were studied and the reaction conditions were optimized to reach satisfactory yields of the target glycols. Some transformations of the γ-glycols were studied. It was found that the reaction of 1-(2-ethoxyethyl)-4-(3-hydroxyprop-1-yn-1-yl)piperidin-4-ol with ethyl bromide involves exclusively the OH group on the quaternary carbon atom to form a monoethyl ether, and the mercury-catalyzed hydration involves cyclization with the elimination of a water molecule from the keto glycol moiety, leading to a spiroketone. It was shown that the catalytic reduction of 1-(2-ethoxyethyl)-4-[2-(1-hydroxycyclohexyl)ethynyl]piperidin-4-ol at atmospheric pressure produces a mixture of a saturated and an unsaturated products in a 1 : 2 ratio. Quantum-chemical calculations of the stable conformers of the synthesized asymmetric acetylenic γ-glycols were performed by the RHF/STO-3G method with geometry optimization using Gaussian 09 software.

cyclization , ether , glycol , hydration , ketoglycol , ketone , oxalate , piperidine , propargyl alcohol , spiroketone

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Al-Farabi Kazakh National University, Almaty, 050040, Kazakhstan

Al-Farabi Kazakh National University

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