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Rearrangement-cyclization of dialkyl(4-hydroxybut-2-ynyl)(3-phenylprop-2-enyl)ammonium bromides in the presence of aqueous alkali
- Authors: Gevorgyan H.R.1,2, Chukhajian E.O.1
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Affiliations:
- Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia
- National Polytechnic University of Armenia
- Issue: Vol 60, No 5 (2024)
- Pages: 627-631
- Section: Articles
- URL: https://permmedjournal.ru/0514-7492/article/view/685342
- DOI: https://doi.org/10.31857/S0514749224050066
- EDN: https://elibrary.ru/RCXSZY
- ID: 685342
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Abstract
Dialkyl(4-hydroxybut-2-ynyl)(3-phenylprop-2-enyl) ammonium bromides in the presence of catalytic amounts of aqueous alkali do not undergo intramolecular [4+2] cyclization of the diene synthesis type, since 3-phenylprop-2-enyl group does not participate in the reaction as a diene fragment, and the initinal salts are formed again. In the presence of twofold amounts of aqueous alkali, contrary to our expectations, the salts undergo Stevens rearrangement with transfer of the reaction center in both the host and migrating groups, followed by intramolecular cyclization rather than intramolecular cyclization–recyclization.
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About the authors
H. R. Gevorgyan
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia; National Polytechnic University of Armenia
Author for correspondence.
Email: hasmikgevorgyan973@gmail.com
ORCID iD: 0009-0006-8615-5434
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia, Institute of Organic Chemistry
Armenia, prosp. Azatutyana, 26, Yerevan, 0014; st. Teryan 105, Yerevan, 0009E. O. Chukhajian
Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia
Email: hasmikgevorgyan973@gmail.com
ORCID iD: 0000-0003-0666-3481
Institute of Organic Chemistry
Armenia, prosp. Azatutyana, 26, Yerevan, 0014References
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