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Synthetic routes to 3(5)-phosphonylated pyrazoles

Nataliya Sergeevna Goulioukina 1
Nataliya Sergeevna Goulioukina
, 
Nikolay Nikolaevich Makukhin 1
Nikolay Nikolaevich Makukhin
, 
1 Lomonosov Moscow State University, Faculty of Chemistry
Published 30 November 2015
Communication , Volume 85, Issue 7, 667-683
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Goulioukina N. S., Makukhin N. N., Beletskaya I. P. Synthetic routes to 3(5)-phosphonylated pyrazoles // Russian Chemical Reviews. 2016. Vol. 85. No. 7. pp. 667-683.
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Goulioukina N. S., Makukhin N. N., Beletskaya I. P. Synthetic routes to 3(5)-phosphonylated pyrazoles // Russian Chemical Reviews. 2016. Vol. 85. No. 7. pp. 667-683.
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TY - JOUR
DO - 10.1070/RCR4579
UR - https://rcr.colab.ws/publications/10.1070/RCR4579
TI - Synthetic routes to 3(5)-phosphonylated pyrazoles
T2 - Russian Chemical Reviews
AU - Goulioukina, Nataliya Sergeevna
AU - Makukhin, Nikolay Nikolaevich
AU - Beletskaya, Irina Petrovna
PY - 2016
DA - 2015/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 667-683
IS - 7
VL - 85
ER -
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@article{2016_Goulioukina,
author = {Nataliya Sergeevna Goulioukina and Nikolay Nikolaevich Makukhin and Irina Petrovna Beletskaya},
title = {Synthetic routes to 3(5)-phosphonylated pyrazoles},
journal = {Russian Chemical Reviews},
year = {2016},
volume = {85},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4579},
number = {7},
pages = {667--683},
doi = {10.1070/RCR4579}
}
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Goulioukina, Nataliya Sergeevna, et al. “Synthetic routes to 3(5)-phosphonylated pyrazoles.” Russian Chemical Reviews, vol. 85, no. 7, Nov. 2016, pp. 667-683. https://rcr.colab.ws/publications/10.1070/RCR4579.
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Abstract

This review comprehensively covers the currently available synthetic routes to 3(5)-phosphonylated pyrazoles. There are demonstrated significant advances in this field over the last 10--15 years caused by the use of the Bestmann--Ohira reagent [as well as (diazomethyl)phosphonates and phosphonylated hydrazonoyl halides] in reactions with diverse dipolarophiles. 1,3-Dipolar cycloaddition of diazo compounds to $\alpha$,$\beta$-unsaturated phosphonates as well as intramolecular heterocyclization of (1-diazoallyl)phosphonates and (3-diazo-1-propenyl)phosphonates are discussed. Synthetic potential of cyclocondensation of organophosphorus 1,3-dielectrophilic compounds with hydrazines is shown. Ways to introduce a phosphonate group into the pyrazole ring are considered. Examples of chemical transformations of 3(5)-phosphonylated pyrazoles are reported.

The bibliography includes 88 references.