volume 9 issue 7 pages 1955-1959

Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones

Lepeng Chen 1
Ningning Lv 1
Qianqian Zhen 1
Zhongyan Chen 1
Jing Yuan Ge 1
Jiu-Xi Chen 1
Publication typeJournal Article
Publication date2022-02-16
scimago Q1
wos Q1
SJR1.068
CiteScore8.2
Impact factor4.7
ISSN20524110, 20524129
Organic Chemistry
Abstract
Developing efficient methods to accommodate azaheterocycles has been a hotspot field in organic synthesis. Herein, we disclose a facile and expeditious avenue to synthesize 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones via a nickel-catalyzed addition, condensation, and annulation sequence of commercially available dinitriles and boronic acids with hydrazine hydrochlorides. The conversion features a high step economy and good functional group tolerance. The synthetic utility of this methodology is demonstrated by scaled-up reaction and construction of a biologically active triazole biheteroaryl skeleton in a one-pot manner from simple feedstocks.
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Chen L. et al. Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones // Organic Chemistry Frontiers. 2022. Vol. 9. No. 7. pp. 1955-1959.
GOST all authors (up to 50) Copy
Chen L., Lv N., Zhen Q., Chen Z., Ge J. Y., Chen J. Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones // Organic Chemistry Frontiers. 2022. Vol. 9. No. 7. pp. 1955-1959.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1039/d2qo00036a
UR - https://xlink.rsc.org/?DOI=D2QO00036A
TI - Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones
T2 - Organic Chemistry Frontiers
AU - Chen, Lepeng
AU - Lv, Ningning
AU - Zhen, Qianqian
AU - Chen, Zhongyan
AU - Ge, Jing Yuan
AU - Chen, Jiu-Xi
PY - 2022
DA - 2022/02/16
PB - Royal Society of Chemistry (RSC)
SP - 1955-1959
IS - 7
VL - 9
SN - 2052-4110
SN - 2052-4129
ER -
BibTex |
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BibTex (up to 50 authors) Copy
@article{2022_Chen,
author = {Lepeng Chen and Ningning Lv and Qianqian Zhen and Zhongyan Chen and Jing Yuan Ge and Jiu-Xi Chen},
title = {Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones},
journal = {Organic Chemistry Frontiers},
year = {2022},
volume = {9},
publisher = {Royal Society of Chemistry (RSC)},
month = {feb},
url = {https://xlink.rsc.org/?DOI=D2QO00036A},
number = {7},
pages = {1955--1959},
doi = {10.1039/d2qo00036a}
}
MLA
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MLA Copy
Chen, Lepeng, et al. “Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones.” Organic Chemistry Frontiers, vol. 9, no. 7, Feb. 2022, pp. 1955-1959. https://xlink.rsc.org/?DOI=D2QO00036A.