Guanidine Hydrochloride Catalyzed One-Pot Multi-Component Synthesis of Pyrazolopyranopyrimidine

被引：5

作者：

Barkule, Angad B. ^{[1
]}

Gadkari, Yatin U. ^{[2
]}

Salim, Simren S. ^{[1
]}

Lomte, Savita B. ^{[1
]}

Telvekar, Vikas N. ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, India

[2] Inst Chem Technol Indian Oil, Dept Pharmaceut Sci & Technol, Odisha Campus, Bhubaneswar 751013, India

来源：

CHEMISTRYSELECT | 2023年 / 8卷 / 21期

关键词：

Aqueous condition; guanidine hydrochloride; multi-component reaction; pyrazolopyranopyrimidine; recyclability; 4-COMPONENT SYNTHESIS; EFFICIENT CATALYST; GREEN; DERIVATIVES; ORGANOCATALYST; PROTOCOL; DESIGN;

D O I：

10.1002/slct.202300990

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An expeditious and highly efficient methodology for the synthesis of pyrazolopyranopyrimidine under aqueous conditions is reported using guanidine hydrochloride as a catalyst. One-pot multicomponent synthesis from aryl/heterocyclic aldehyde, ethyl acetoacetate, barbituric acid, and hydrazine hydrate to give the final compound in moderate to excellent yield. The recyclability (up to 4 cycles), safe, low cost, and wide stability profile of guanidine hydrochloride fulfil the ideal properties of the catalyst. The current protocol shows several advantages such as its environmentally benign nature, shorter reaction time, high yield, simple work-up procedure, broad substrate tolerance, absence of hazardous organic solvent, etc.

引用

页数：6

共 54 条

[1] Synthesis, Antimicrobial and Antioxidant Activities of Novel 7-thioxo-4,6,7,8-tetrahydro-pyrazolo[4 ',3 ':5,6]pyrano[2,3-d]pyrinnidin-5(1H)-ones Derived by SDS Catalyzed Multicomponent Reactions in Aqueous Micellar Media
Ahanthem, Dini
Singh, Shyamkesho M.
Laitonjam, Warjeet S.
[J]. NATURAL PRODUCTS JOURNAL, 2018, 8 (03) : 228 - 238
[2] Ultrasound-Assisted β-Cyclodextrin Catalyzed One-Pot Cascade Synthesis of Pyrazolopyranopyrimidines in Water
Akolkar, Satish V.
Kharat, Narendra D.
Nagargoje, Amol A.
Subhedar, Dnyaneshwar D.
Shingate, Bapurao B.
[J]. CATALYSIS LETTERS, 2020, 150 (02) : 450 - 460
[3] Organo-nanocatalysis: An emergent green methodology for construction of bioactive oxazines and thiazines under ultrasonic irradiation
Ansari, Mohd Danish
Sagir, Hozeyfa
Yadav, Vijay B.
Yadav, Neetu
Verma, Ankit
Siddiqui, I. R.
[J]. JOURNAL OF MOLECULAR STRUCTURE, 2019, 1196 : 54 - 57
[4] Synthesis of Benzo[b]furan Derivatives via S8-Nano particles/β-cyclodextrin: An Environmentally Friendly Approach
Ansari, Mohd Danish
Sagir, Hozeyfa
Yadav, Vijay B.
Yadav, Neetu
Siddiqui, I. R.
[J]. CHEMISTRYSELECT, 2018, 3 (19): : 5326 - 5329
[5] Microwave-assisted synthesis of pyrimidine libraries
Bagley, MC
Hughes, DD
Lubinu, MC
Merritt, EA
Taylor, PH
Tomkinson, NCO
[J]. QSAR & COMBINATORIAL SCIENCE, 2004, 23 (10): : 859 - 867
[6] Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents
Bandgar, Babasaheb P.
Gawande, Shrikant S.
Bodade, Ragini G.
Gawande, Nalini M.
Khobragade, Chandrahasya N.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (24) : 8168 - 8173
[7] Green and Efficient Synthesis of 1, 2, 4-Triazolidine-3-thiones using Guanidine Hydrochloride as a Recyclable Catalyst under the Aqueous Condition
Barkule, Angad B.
Gadkari, Yatin U.
Telvekar, Vikas N.
[J]. LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (09) : 683 - 688
[8] One-Pot Multicomponent Synthesis of 3-Methyl-4-(Hetero)Arylmethylene Isoxazole-5(4H)-Ones Using Guanidine Hydrochloride as the Catalyst under Aqueous Conditions
Barkule, Angad B.
Gadkari, Yatin U.
Telvekar, Vikas N.
[J]. POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (09) : 5870 - 5881
[9] ISOLATION AND IDENTIFICATION OF ANISALDEHYDE AND 3 ALKALOIDS FROM LEAVES OF THALICTRUM-MINUS VAR MICROPHYLLUM
BASER, KHC
[J]. JOURNAL OF NATURAL PRODUCTS, 1982, 45 (06): : 704 - 706
[10] Synthesis, in vitro antimicrobial and cytotoxic activities of novel pyrimidine-benzimidazol combinations
Chen, Peng-Ju
Yang, Ang
Gu, Yi-Fei
Zhang, Xiao-Song
Shao, Kun-Peng
Xue, Deng-Qi
He, Peng
Jiang, Teng-Fei
Zhang, Qiu-Rong
Liu, Hong-Min
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (12) : 2741 - 2743

← 1 2 3 4 5 6 →