A convenient synthesis of new phosphonomethyl-containing 4,5-dihydropyridazin-3(2H)-ones

被引：0

作者：

Bejaoui, Oumayma ^{[1
]}

Abdelli, Abderrahmen ^{[1
]}

M'rabet, Hedi ^{[1
]}

Moreau, Xavier ^{[2
]}

Efrit, Mohamed Lotfi ^{[1
]}

Prim, Damien ^{[2
]}

机构：

[1] Univ Tunis El Manar, Fac Sci Tunis, Lab Synth Organ & Heterocycl Select Evaluat Act Bi, LR17ES01, Tunis 2092, Tunisia

[2] Univ Paris Saclay, Inst Lavoisier Versailles, UVSQ, CNRS, F-78035 Versailles, France

来源：

MENDELEEV COMMUNICATIONS | 2023年 / 33卷 / 05期

关键词：

pyridazin-3(2H)-ones; phosphonates; nitroalkanes; g-keto ester; Michael addition; Nef reaction;

D O I：

10.1016/j.mencom.2023.09.016

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An expedient access to novel 4-phosphonomethyl-containing 2,6-disubstituted 4,5-dihydropyridazin-3(2H)-ones involves the reaction of b-phosphono g '-keto ester intermediates with hydrazines. The construction of the pyridazinone ring allows the installation of various substituents at the positions 2 and 6 as well as a valuable 4-positioned phosphonomethyl fragment. CO2Et PO(OEt)2 2 steps R1 R2 N N 10 examples 76-88% yields O O P OEt OEt

引用

页码：640 / 641

页数：2

共 27 条

[1] Abdelbaset M.S., 2019, J ADV BIOMED PHARM S, V2, P19, DOI DOI 10.21608/JABPS.2018.5283.1023
[2] Synthesis and evaluation of new phosphonated δ-lactam and glutarimide derivatives as angiotensin converting enzyme inhibitors
Abdelli, Abderrahmen
Bejaoui, Oumayma
Bougatef, Hajer
Ouni, Sarra
Sila, Assaad
M'rabet, Hedi
Moreau, Xavier
Efrit, Mohamed Lotfi
Prim, Damien
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (01) : 96 - 105
[3] Versatile approach to densely substituted isoxazolines and pyrazolines: Focus on a quaternary carbon center as a constitutive feature
Abdelli, Abderrahmen
Gharsa, Haythem
Jmai, Momtez
Gaucher, Anne
Efrit, Mohamed Lotfi
M'rabet, Hedi
Prim, Damien
[J]. TETRAHEDRON LETTERS, 2020, 61 (23)
[4] A convenient synthesis of phosphonomethyl α,β-unsaturated γ-lactams
Abdelli, Abderrahmen
Efrit, Mohamed Lotfi
Gaucher, Anne
M'rabet, Hedi
Prim, Damien
[J]. TETRAHEDRON LETTERS, 2015, 56 (40) : 5397 - 5400
[5] Synthesis of 1,2,4-triazolopyridazines, isoxazolofuropyridazines, and tetrazolopyridazines as antimicrobial agents
Abu-Hashem, Ameen A.
Fathy, Usama
Gouda, Moustafa A.
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (09) : 3461 - 3474
[6] Synthesis and biological evaluation of pyridazinone derivatives as selective COX-2 inhibitors and potential anti-inflammatory agents
Ahmed, Eman M.
Kassab, Asmaa E.
El-Malah, Afaf A.
Hassan, Marwa S. A.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 171 : 25 - 37
[7] New, simple and versatile synthesis of 4,6-disubstituted pyridazin-3(2H)-ones
Albrecht, Anna
Koszuk, Jacek
Kobucinski, Michal
Janecki, Tomasz
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (07) : 1197 - 1200
[8] SYNTHESIS AND ANTIBACTERIAL EVALUATION OF (E)-5-ARYLIDENE-6-METHYL-4,5-DIHYDROPYRIDAZIN-3(2)-THIONE DERIVATIVES
Alghamdi, Saad
Imran, Mohd
Kamal, Mehnaz
Asif, Mohammad
[J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2021, 55 (09) : 915 - 919
[9] Asif M., 2020, INT J NEW CHEM, V7, P303
[10] Asif M., 2019, J. Chem. Rev, V2, P57

← 1 2 3 →