Synthesis of Pyrazolopyranopyrimidine and Dihydropyrano[2,3-c]Pyrazole Derivatives Using Fe3O4@THAM-Piperazine as a Superparamagnetic Nanocatalyst under Green Condition

被引：6

作者：

Mir, Fatemeh ^{[1
]}

Hazeri, Nourallah ^{[1
]}

Maghsoodlou, Malek Taher ^{[1
]}

Lashkari, Mojtaba ^{[2
]}

机构：

[1] Univ Sistan & Baluchestan, Fac Sci, Dept Chem, POB 98135-674, Zahedan, Iran

[2] Velayat Univ, Fac Sci, Iranshahr, Iran

来源：

POLYCYCLIC AROMATIC COMPOUNDS | 2023年 / 43卷 / 06期

关键词：

Dihydropyrano[2; 3-c]pyrazole; Fe3O4@THAM-piperazine; green condition; pyrazolopyranopyrimidine; superparamagnetic nanocatalyst; ONE-POT SYNTHESIS; 4-COMPONENT SYNTHESIS; EFFICIENT CATALYST; MULTICOMPONENT REACTIONS; NANOPARTICLES; ACID; PROTOCOL;

D O I：

10.1080/10406638.2022.2101488

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this article, a new and simple procedure was designed for the preparation of pyrazolopyranopyrimidine and dihydropyrano[2,3-c]pyrazole derivatives using the reaction between hydrazine hydrate, aryl aldehydes, malononitrile or barbituric acid, and ethyl acetoacetate using Fe3O4@THAM-piperazine as a solid nanocatalyst in a solution of water and ethanol at 60 degrees C. The present process offers advantages like easy workup, short reaction time, non-toxicity, and the use of green solvent. Moreover, recyclability studies were carried out that showed a high potential of reusing and recovering capability.

引用

页码：5375 / 5390

页数：16

共 50 条

[11] Magnetized melamine-modified polyacrylonitrile (PAN@melamine/Fe3O4) organometallic nanomaterial: Preparation, characterization, and application as a multifunctional catalyst in the synthesis of bioactive dihydropyrano [2,3-c]pyrazole and 2-amino-3-cyano 4H-pyran derivatives
Hassanzadeh-Afruzi, Fereshte
Dogari, Haniyeh
Esmailzadeh, Farhad
Maleki, Ali
APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (10)
[12] Pyrrolidine-Catalyzed Four-Component One-Pot Synthesis of Dihydropyrano[2,3-C]Pyrazole Derivatives
Wang Liju
Ablajan, Keyume
CURRENT ORGANIC SYNTHESIS, 2014, 11 (02) : 310 - 316
[13] Green synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles] using Fe3O4@l-arginine as a robust and reusable catalyst
Ghasemzadeh, Mohammad Ali
Mirhosseini-Eshkevari, Boshra L.
Abdollahi-Basir, Mohammad Hossein
BMC CHEMISTRY, 2019, 13 (01)
[14] DABA MNPs: a new and efficient magnetic bifunctional nanocatalyst for the green synthesis of biologically active pyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives
Karami, Shahriar
Dekamin, Mohammad G.
Valiey, Ehsan
Shakib, Peyman
NEW JOURNAL OF CHEMISTRY, 2020, 44 (33) : 13952 - 13961
[15] Tungstic acid-functionalized Fe3O4@TiO2: preparation, characterization and its application for the synthesis of pyrano[2,3-c]pyrazole derivatives as a reusable magnetic nanocatalyst
Gholtash, Jamileh Etemad
Farahi, Mahnaz
RSC ADVANCES, 2018, 8 (71): : 40962 - 40967
[16] Synthesis of benzo[b]pyran and pyrano[2,3-d]pyrimidine derivatives using a new superparamagnetic nanocatalyst Fe3O4@gly@Furfural@Co(NO3)2
Keshani, Raheleh
Hazeri, Nourallah
Faroughi Niya, Homayoun
Fatahpour, Maryam
RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (08) : 3461 - 3479
[17] Applications of a novel nano magnetic catalyst in the synthesis of 1,8-dioxo-octahydroxanthene and dihydropyrano[2,3-c]pyrazole derivatives
Zolfigol, Mohammad Ali
Ayazi-Nasrabadi, Roya
Baghery, Saeed
Khakyzadeh, Vahid
Azizian, Saeid
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 418 : 54 - 67
[18] Preparation of triazine-based functionalized HY zeolite and its application in the green synthesis of tetrahydrobenzo[b]pyran and 1, 4-dihydropyrano [2, 3-c] pyrazole derivatives as a novel mesoporous recyclable nanocatalyst
Alimohammadi, Elham
Kaveh, Khosravi
Ali, Zolfigol Mohammad
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2022, 19 (12) : 4721 - 4734
[19] BF3 bonded nano Fe3O4 (BF3/MNPs): an efficient magnetically recyclable catalyst for the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives
Abdollahi-Alibeik, Mohammad
Moaddeli, Ali
Masoomi, Kianoosh
RSC ADVANCES, 2015, 5 (91): : 74932 - 74939
[20] An Efficient and Green Synthesis of 6-Amino-3-phenyl-4-aryl-1,4-dihydropyrano [2,3-c]pyrazole-5-carbonitrile Derivatives under Ultrasound Irradiation in Aqueous Medium
Zou, Yi
Hu, Yu
Liu, Hai
Shi, Da-Qing
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (05) : 1174 - 1179

← 1 2 3 4 5 →