The homologous tert-amino effect: a route to fused 2-benzazepine derivatives
Alexander P Gorulya
1
,
Anton V Tverdokhlebov
1
,
Andrey A. Tolmachev
2, 3
,
Oleg V. Shishkin
4
,
Svetlana V. Shishkina
4
1
Enamine Ltd., Alexandra Matrosova str. 23, 01103, Kiev, Ukraine
|
2
Enamine Ltd., Alexandra Matrosova str. 23, 01103 Kiev, Ukraine
|
3
Kiev National Taras Shevchenko University, Volodimirska Str. 62, 01033 Kiev, Ukraine
|
4
STC ‘Institute for Single Crystals’, NAS of Ukraine, 60 Lenina ave., 61001, Kharkiv, Ukraine
|
Publication type: Journal Article
Publication date: 2011-02-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
2-Cyano- and 2-carbethoxy-3-[2-(pyrrolidin-1-ylmethyl)phenyl]acrylonitriles were prepared through either amination of appropriate 3-[2-(bromomethyl)phenyl]acrylonitriles with pyrrolidine or condensation of 2-(pyrrolidin-1-ylmethyl)benzaldehyde with malononitrile and ethyl cyanoacetate. These acrylonitrile derivatives were shown to undergo easy mutual interconversion with 1-(pyrrolidin-1-yl)indane-2-carbonitriles driven by solvent polarity. Upon heating at 140–150 °C both acrylonitrile and indane derivatives were found to give 2,3,5,10,11,11a-hexahydro-1H-pyrrolo[1,2-b][2]benzazepine-11-carbonitriles. All transformations observed were rationalized in the terms of reactions related to the tert-amino effect. Furthermore, the corresponding piperidin-1-yl and azepan-1-yl analogs of the above acrylonitriles and indanes were obtained similarly. By analogy their heating afforded 1,2,3,4,6,11,12,12a-octahydropyrido[1,2-b][2]benzazepine-12-carbonitriles and 7,8,9,10,11,11a, 12,13-octahydro-5H-azepino[1,2-b][2]benzazepine-12-carbonitriles.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
|
|
|
Chemistry of Heterocyclic Compounds
2 publications, 9.52%
|
|
|
Angewandte Chemie - International Edition
2 publications, 9.52%
|
|
|
Angewandte Chemie
2 publications, 9.52%
|
|
|
Organic Letters
2 publications, 9.52%
|
|
|
Chemical Communications
2 publications, 9.52%
|
|
|
Russian Chemical Bulletin
1 publication, 4.76%
|
|
|
ChemistrySelect
1 publication, 4.76%
|
|
|
Chinese Journal of Chemistry
1 publication, 4.76%
|
|
|
Journal of Physical Organic Chemistry
1 publication, 4.76%
|
|
|
Crystal Growth and Design
1 publication, 4.76%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 4.76%
|
|
|
Progress in Heterocyclic Chemistry
1 publication, 4.76%
|
|
|
Organic Reaction Mechanisms
1 publication, 4.76%
|
|
|
RSC Catalysis Series
1 publication, 4.76%
|
|
|
Tetrahedron
1 publication, 4.76%
|
|
|
Mendeleev Communications
1 publication, 4.76%
|
|
|
1
2
|
Publishers
|
1
2
3
4
5
6
7
8
9
|
|
|
Wiley
9 publications, 42.86%
|
|
|
Springer Nature
3 publications, 14.29%
|
|
|
American Chemical Society (ACS)
3 publications, 14.29%
|
|
|
Royal Society of Chemistry (RSC)
3 publications, 14.29%
|
|
|
Elsevier
2 publications, 9.52%
|
|
|
OOO Zhurnal "Mendeleevskie Soobshcheniya"
1 publication, 4.76%
|
|
|
1
2
3
4
5
6
7
8
9
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
21
Total citations:
21
Citations from 2025:
2
(9.52%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Gorulya A. P. et al. The homologous tert-amino effect: a route to fused 2-benzazepine derivatives // Tetrahedron. 2011. Vol. 67. No. 5. pp. 1030-1035.
GOST all authors (up to 50)
Copy
Gorulya A. P., Tverdokhlebov A. V., Tolmachev A. A., Shishkin O. V., Shishkina S. V. The homologous tert-amino effect: a route to fused 2-benzazepine derivatives // Tetrahedron. 2011. Vol. 67. No. 5. pp. 1030-1035.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.tet.2010.11.101
UR - https://doi.org/10.1016/j.tet.2010.11.101
TI - The homologous tert-amino effect: a route to fused 2-benzazepine derivatives
T2 - Tetrahedron
AU - Gorulya, Alexander P
AU - Tverdokhlebov, Anton V
AU - Tolmachev, Andrey A.
AU - Shishkin, Oleg V.
AU - Shishkina, Svetlana V.
PY - 2011
DA - 2011/02/01
PB - Elsevier
SP - 1030-1035
IS - 5
VL - 67
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2011_Gorulya,
author = {Alexander P Gorulya and Anton V Tverdokhlebov and Andrey A. Tolmachev and Oleg V. Shishkin and Svetlana V. Shishkina},
title = {The homologous tert-amino effect: a route to fused 2-benzazepine derivatives},
journal = {Tetrahedron},
year = {2011},
volume = {67},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.tet.2010.11.101},
number = {5},
pages = {1030--1035},
doi = {10.1016/j.tet.2010.11.101}
}
Cite this
MLA
Copy
Gorulya, Alexander P., et al. “The homologous tert-amino effect: a route to fused 2-benzazepine derivatives.” Tetrahedron, vol. 67, no. 5, Feb. 2011, pp. 1030-1035. https://doi.org/10.1016/j.tet.2010.11.101.