Aza-Wittig Reaction with Nitriles: How Carbonyl Function Switches from Reacting to Activating
Publication type: Journal Article
Publication date: 2019-02-07
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
30730148
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Transformations of α-EWG-substituted (electron-withdrawing group, EWG) γ-azidobutyronitriles proceeding via unusual aza-Wittig reactions between the phosphazene and nitrile functions and affording pyrrole-derived iminophosphazenes were developed. α-EWGs were found to control chemoselectivity and, depending on their nature, act as CN group activators (e.g., ester, amide, or nitrile) or competitors (e.g., ketone) in aza-Wittig reactions. To demonstrate the synthetic utility of the obtained iminophosphazenes as N, N-binucleophiles, their transformations into pyrrole-fused systems, pyrrolo[1,2- a]imidazoles and pyrrolo[1,2- a][1,3]diazepines, were carried out.
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Total citations:
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Citations from 2024:
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(19.23%)
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GOST
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Tukhtaev H. B. et al. Aza-Wittig Reaction with Nitriles: How Carbonyl Function Switches from Reacting to Activating // Organic Letters. 2019. Vol. 21. No. 4. pp. 1087-1092.
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Tukhtaev H. B., Ivanov K. L., Bezzubov S. I., Cheshkov D. A., Melnikov M. Y., Melnikov M. Ya., Budynina E. M. Aza-Wittig Reaction with Nitriles: How Carbonyl Function Switches from Reacting to Activating // Organic Letters. 2019. Vol. 21. No. 4. pp. 1087-1092.
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TY - JOUR
DO - 10.1021/acs.orglett.8b04135
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.8b04135
TI - Aza-Wittig Reaction with Nitriles: How Carbonyl Function Switches from Reacting to Activating
T2 - Organic Letters
AU - Tukhtaev, Hamidulla B
AU - Ivanov, Konstantin L
AU - Bezzubov, Stanislav I.
AU - Cheshkov, Dmitry A.
AU - Melnikov, Mikhail Y.
AU - Melnikov, Mikhail Ya
AU - Budynina, Ekaterina M
PY - 2019
DA - 2019/02/07
PB - American Chemical Society (ACS)
SP - 1087-1092
IS - 4
VL - 21
PMID - 30730148
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2019_Tukhtaev,
author = {Hamidulla B Tukhtaev and Konstantin L Ivanov and Stanislav I. Bezzubov and Dmitry A. Cheshkov and Mikhail Y. Melnikov and Mikhail Ya Melnikov and Ekaterina M Budynina},
title = {Aza-Wittig Reaction with Nitriles: How Carbonyl Function Switches from Reacting to Activating},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.8b04135},
number = {4},
pages = {1087--1092},
doi = {10.1021/acs.orglett.8b04135}
}
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MLA
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Tukhtaev, Hamidulla B., et al. “Aza-Wittig Reaction with Nitriles: How Carbonyl Function Switches from Reacting to Activating.” Organic Letters, vol. 21, no. 4, Feb. 2019, pp. 1087-1092. https://pubs.acs.org/doi/10.1021/acs.orglett.8b04135.