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Modification of g-Aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines

Tat'yana Evgen'evna Glotova 1
Tat'yana Evgen'evna Glotova
, 
Marina Yu Dvorko 1
Marina Yu Dvorko
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Dmitrii Andreevich Shabalin 1
Dmitrii Andreevich Shabalin
, 
Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2012.11.012
Published 2012-11-07
Communication , Volume 22, Issue 6, 314-316
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Glotova T. E. et al. Modification of g-Aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines // Mendeleev Communications. 2012. Vol. 22. No. 6. pp. 314-316.
GOST all authors (up to 50) Copy
Glotova T. E., Dvorko M. Yu., Ushakov I. A., Shabalin D. A., Schmidt E. Y., Trofimov B. A. Modification of g-Aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines // Mendeleev Communications. 2012. Vol. 22. No. 6. pp. 314-316.
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TY - JOUR
DO - 10.1016/j.mencom.2012.11.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.012
TI - Modification of g-Aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines
T2 - Mendeleev Communications
AU - Glotova, Tat'yana Evgen'evna
AU - Dvorko, Marina Yu
AU - Ushakov, Igor Alekseevich
AU - Shabalin, Dmitrii Andreevich
AU - Schmidt, Elena Yur'evna
AU - Trofimov, Boris Aleksandrovich
PY - 2012
DA - 2012/11/07
PB - Mendeleev Communications
SP - 314-316
IS - 6
VL - 22
ER -
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@article{2012_Glotova,
author = {Tat'yana Evgen'evna Glotova and Marina Yu Dvorko and Igor Alekseevich Ushakov and Dmitrii Andreevich Shabalin and Elena Yur'evna Schmidt and Boris Aleksandrovich Trofimov},
title = {Modification of g-Aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.012},
number = {6},
pages = {314--316},
doi = {10.1016/j.mencom.2012.11.012}
}
MLA
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Glotova, Tat'yana Evgen'evna, et al. “Modification of g-Aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines.” Mendeleev Communications, vol. 22, no. 6, Nov. 2012, pp. 314-316. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.012.

Abstract

Primary N–C adducts of g-aminobutyric acid (GABA) to acylacetylenes undergo mild stereoselective C-vinylation by another acylacetylene molecule to afford (2E,4Z)-4-acyl-5-aminoalka-2,4-dien-1-one-type diadducts in 83–92% yields. The latter cyclize to acylpyridines in up to 89% yields with the C–N bond cleavage in the GABA moiety and elimination of g-butyrolactone.

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