Open Access
Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)4 and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et2Zn
Rita N. Kadikova
1, 2, 3, 4
,
Ilfir R Ramazanov
1
,
Azat M. Gabdullin
1, 2, 3, 4
,
Oleg S. Mozgovoj
1, 2, 3, 4
,
Usein M Dzhemilev
1
Publication type: Journal Article
Publication date: 2020-05-07
scimago Q1
wos Q2
SJR: 0.777
CiteScore: 7.6
Impact factor: 4.6
ISSN: 20462069
PubMed ID:
35515579
General Chemistry
General Chemical Engineering
Abstract
The Ti(O-iPr)4 and EtMgBr-catalyzed regio and stereoselective carbocyclization of N-allyl-substituted 2-alkynylamines with Et2Zn, followed by deuterolysis or hydrolysis, affords the corresponding methylenepyrrolidine derivatives in high yields. It was found that Ti–Mg-catalyzed carbocyclization of N-allyl-substituted 2-alkynylamines with Et2Zn is equally selective in dichloromethane, hexane, toluene, and diethyl ether. The reaction was tolerant to the presence of aryl, alkyl, trimethylsilyl, methoxymethyl and aminomethyl substituents on the alkyne. A selective method was proposed for the preparation of bis-pyrrolidine derivatives using Ti–Mg-catalyzed carbocyclization of bis-allylpropargyl amines with Et2Zn.
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7
Total citations:
7
Citations from 2024:
5
(71%)
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Kadikova R. N. et al. Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)4 and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et2Zn // RSC Advances. 2020. Vol. 10. No. 30. pp. 17881-17891.
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Kadikova R. N., Ramazanov I. R., Gabdullin A. M., Mozgovoj O. S., Dzhemilev U. M. Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)4 and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et2Zn // RSC Advances. 2020. Vol. 10. No. 30. pp. 17881-17891.
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RIS
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TY - JOUR
DO - 10.1039/d0ra02677h
UR - https://xlink.rsc.org/?DOI=D0RA02677H
TI - Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)4 and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et2Zn
T2 - RSC Advances
AU - Kadikova, Rita N.
AU - Ramazanov, Ilfir R
AU - Gabdullin, Azat M.
AU - Mozgovoj, Oleg S.
AU - Dzhemilev, Usein M
PY - 2020
DA - 2020/05/07
PB - Royal Society of Chemistry (RSC)
SP - 17881-17891
IS - 30
VL - 10
PMID - 35515579
SN - 2046-2069
ER -
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@article{2020_Kadikova,
author = {Rita N. Kadikova and Ilfir R Ramazanov and Azat M. Gabdullin and Oleg S. Mozgovoj and Usein M Dzhemilev},
title = {Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)4 and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et2Zn},
journal = {RSC Advances},
year = {2020},
volume = {10},
publisher = {Royal Society of Chemistry (RSC)},
month = {may},
url = {https://xlink.rsc.org/?DOI=D0RA02677H},
number = {30},
pages = {17881--17891},
doi = {10.1039/d0ra02677h}
}
Cite this
MLA
Copy
Kadikova, Rita N., et al. “Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)4 and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et2Zn.” RSC Advances, vol. 10, no. 30, May. 2020, pp. 17881-17891. https://xlink.rsc.org/?DOI=D0RA02677H.