Rearrangement-cyclization of dialkyl(4-hydroxybut-2-ynyl)(3-phenylprop-2-enyl)ammonium bromides in the presence of aqueous alkali

H. R. Gevorgyan; Геворгян Асмик Робертовна; E. O. Chukhajian; Чухаджян Эмма Овсеповна

doi:10.31857/S0514749224050066

Rearrangement-cyclization of dialkyl(4-hydroxybut-2-ynyl)(3-phenylprop-2-enyl)ammonium bromides in the presence of aqueous alkali

作者: Gevorgyan H.R.¹^,2, Chukhajian E.O.¹
隶属关系:
1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia
2. National Polytechnic University of Armenia
期: 卷 60, 编号 5 (2024)
页面: 627-631
栏目: Articles
URL: https://vestnikugrasu.org/0514-7492/article/view/685342
DOI: https://doi.org/10.31857/S0514749224050066
EDN: https://elibrary.ru/RCXSZY
ID: 685342

如何引用文章

全文:

开放存取

##reader.subscriptionAccessGranted##
受限制的访问

订阅存取

详细
全文:
作者简介
参考
补充文件
统计

详细

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.

关键词

dialkyl(4-hydroxybut-2-ynyl)(3-phenylprop-2-enyl)ammonium bromides, Stevens rearrangement, intramolecular cyclization, recyclization, basic catalysis, diene fragment

全文:

作者简介

H. Gevorgyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia; National Polytechnic University of Armenia

编辑信件的主要联系方式.
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

亚美尼亚, prosp. Azatutyana, 26, Yerevan, 0014; st. Teryan 105, Yerevan, 0009

E. 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

亚美尼亚, prosp. Azatutyana, 26, Yerevan, 0014

参考

Чухаджян Э.О., Шахатуни К.Г., Чухаджян Эл.О. Химия в интересах устойчив. развития. 2013, 21, 279–290. [Chukhajian E.O., Shahkhatuni K.G., Chukhajian El.O. Chem. Sustainable Dev. 2013, 21, 263– 274.]
Бабаян А.Т., Чухаджян Э.О., Чухаджян Эл.О., Бабаян Р.П. ЖOрХ, 1977, 13, 518–522.
Бабаян А.Т., Тагмазян K.Ц., Черкезян А.А. ЖОрХ. 1973, 9, 1149–1155.
Чухаджян Э.О., Чухаджян Эл.О., Манасян Л.А., Бабаян А.Т. Арм. хим.ж., 1981, 34, 46–51.
Тагмазян K.Ц., Торосян Г.О., Бабаян А.Т. ЖОрХ. 1974, 10, 2082–2088.
Чухаджян Э.О., Айрапетян Л.В., Чухаджян Эл.О., Паносян Г.А. ХГС, 2012, 9, 1410–1417. [Chukhajian, E.O., Ayrapetyan, L.V., Chukhajian, El.O., Panosyan, H.A. Chem. Heterocycl. Compd., 2012, 48, 1314–1320.] doi: 10.1007/s10593-012-1138-4
Чухаджян Э.О., Айрапетян Л.В., Чухаджян Эл.О., Паносян Г.А. ХГС, 2013, 1367–1374. [Chukhajian, E.O., Ayrapetyan, L.V., Chukhajian, El.O., Panosyan, H.A. Chem. Heterocycl. Compd. 2013, 49, 1274–1280.] doi: 10.1007/s10593-013-1375-1
Чухаджян Э.О., Айрапетян Л.В., Шахатуни К.Г., Чухаджян Э.О., Мкртчян А.С., Паносян Г.А. ЖОрХ. 2019, 55, 373–379. [Chukhajian, E.O., Ayrapetyan, L.V., Shahkhatuni, K.G., Chukhajian, El.O., Mkrtchyan, H.S., Panosyan, H.A. Russ. J. Org. Chem., 2019, 55, 319–324.]
Chukhajian E.O., Gevorkyan H.R., E.O. Chukhajian, K.G. Shahkhatuni, H.A. Panosyan, R.A. Tamazyan. J. Heterocycl. Chem., 2003, 40, 1059–1063. doi: 10.1002/jhet.5570400614
Чухаджян Э.O., Геворкян А.Р., Шахатуни К.Г., Чухаджян Эл.О., Паносян Г.А. ЖОрХ, 2019, 55, 4, 566–572. [Chukhajian, E.O., Gevorgyan, H.R., Shahkhatuni, K.G., Chukhajian, El.O., Panosyan, H.A. Russ. J. Org. Chem., 2019, 55, 473–478.] doi: 10.1134/S1070428019040092
Чухаджян Э.О., Габриелян А.С., Чухаджян Эл.О., Шахатуни К.Г., Паносян. Г.А. ХГС, 2011, 513–520. [Chukhadjian, E.O., Gabrielyan, A.S., Chukhadjian, El.O., Shahkhatuni, K.G., Panosyan, H.A. Chem. Heterocycl. Compd., 2011, 47, 418–424. doi: 10.1007/s10593-011-0775-3].
Чухаджян Э.О., Геворкян А.Р., Чухаджян Эл.О., Шахатуни К.Г. ЖОрХ, 2000, 36, 1304. [Chukhad-zhyan, E.O., Gevorkyan, A.R., Chukhadzhyan, El.O., Shakhatuni, K.G., Russ. J. Org.Chem., 2000, 36, 1263].
Schaefer J.P., Higgins J.G., Shenoy P.K. Org. Synth. 1968, 48, 51. doi: 10.15227/orgsyn.048.0051