A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]pyridazin-4(1H)-ones
Publication type: Journal Article
Publication date: 2015-05-08
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A one-pot copper(II)-catalyzed tandem synthesis of 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones from N-aminopyrroles was developed. This tandem reaction involves a Conrad–Limpach-type reaction, including the thermal condensation of N-aminopyrroles with the carbonyl group of β-oxo esters followed by the cyclization of Schiff base intermediates. Compared to the traditional Conrad–Limpach quinoline synthesis, we herein successfully applied copper(II) as a catalyst in this transformation to furnish 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones for the first time. Most of the substrates bearing electron-donating (EDG) and electron-withdrawing (EWG) groups worked well with this procedure. The corresponding products could be converted directly into diverse pyrrolo[1,2-b]pyridazine for drug discovery and materials science.
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Tan C. et al. A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]pyridazin-4(1H)-ones // European Journal of Organic Chemistry. 2015. Vol. 2015. No. 17. pp. 3656-3660.
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Tan C., Xiang H., He Q., Yang C. A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]pyridazin-4(1H)-ones // European Journal of Organic Chemistry. 2015. Vol. 2015. No. 17. pp. 3656-3660.
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TY - JOUR
DO - 10.1002/ejoc.201500422
UR - https://doi.org/10.1002/ejoc.201500422
TI - A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]pyridazin-4(1H)-ones
T2 - European Journal of Organic Chemistry
AU - Tan, Cun
AU - Xiang, Haoyue
AU - He, Qian
AU - Yang, Chunhao
PY - 2015
DA - 2015/05/08
PB - Wiley
SP - 3656-3660
IS - 17
VL - 2015
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2015_Tan,
author = {Cun Tan and Haoyue Xiang and Qian He and Chunhao Yang},
title = {A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]pyridazin-4(1H)-ones},
journal = {European Journal of Organic Chemistry},
year = {2015},
volume = {2015},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/ejoc.201500422},
number = {17},
pages = {3656--3660},
doi = {10.1002/ejoc.201500422}
}
Cite this
MLA
Copy
Tan, Cun, et al. “A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]pyridazin-4(1H)-ones.” European Journal of Organic Chemistry, vol. 2015, no. 17, May. 2015, pp. 3656-3660. https://doi.org/10.1002/ejoc.201500422.