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Molecules 2016, 21(7), 848; doi:10.3390/molecules21070848

Ultrasonic Synthesis, Molecular Structure and Mechanistic Study of 1,3-Dipolar Cycloaddition Reaction of 1-Alkynylpyridinium-3-olate and Acetylene Derivatives

1
Department of Chemistry, Faculty of Science, Taibah University, Yanbu branch, Yanbu 00000, Saudi Arabia
2
Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo 11757, Egypt
3
Department of Chemistry, College of Science & Arts, King Abdulaziz University, P.O. Box 344, Rabigh 21911, Saudi Arabia
4
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: Mark A. Rizzacasa
Received: 10 May 2016 / Revised: 20 June 2016 / Accepted: 23 June 2016 / Published: 29 June 2016
(This article belongs to the Special Issue Pericyclic Reactions)
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Abstract

Regioselectively, ethyl propiolate reacted with 1-(propergyl)-pyridinium-3-olate to give two regioisomers; ethyl 4-oxo-8-(prop-2-ynyl)-8-aza-bicyclo(3.2.1)octa-2,6-diene-6-carboxylate 4, ethyl 2-oxo-8-(prop-2-ynyl)-8-aza-bicyclo(3.2.1)octa-3,6-diene-6-carboxylate 5 as well as ethyl 2,6-dihydro-6-(prop-2-ynyl)furo(2,3-c)pyridine-3-carboxylate 6. The obtained compounds were identified by their spectral (IR, mass and NMR) data. Moreover, DFT quantum chemical calculations were used to study the mechanism of the cycloaddition reaction. The regioselectivity was explained using transition state calculations, where the calculations agreed with the formation of products 4 and 5 in almost the same ratio. The reaction was also extended for diphenylaceylene as dipolarophile to give only two products instead of three. View Full-Text
Keywords: ultrasonic synthesis; 1,3-dipolar cycloaddition; molecular structure; reaction mechanism ultrasonic synthesis; 1,3-dipolar cycloaddition; molecular structure; reaction mechanism
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Aboelnaga, A.; Hagar, M.; Soliman, S.M. Ultrasonic Synthesis, Molecular Structure and Mechanistic Study of 1,3-Dipolar Cycloaddition Reaction of 1-Alkynylpyridinium-3-olate and Acetylene Derivatives. Molecules 2016, 21, 848.

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