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volume 10 issue 30 pages 17881-17891

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 typeJournal Article
Publication date2020-05-07
scimago Q1
wos Q2
SJR0.777
CiteScore7.6
Impact factor4.6
ISSN20462069
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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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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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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.