Glycerol: A Promising Benign Solvent for Catalyst-free One-pot Multi-component Synthesis of 1H-Pyrozolo[1,2-b]phthalazine-5,10-diones and 2H-Indazolo[2,1-b]phthalazine-triones Under Controlled Microwaves Irradiation

被引:8
作者
Zaky, Omnyia Said [1 ]
Selim, Maghraby Ali [1 ]
Ebied, Manal Makboul [1 ]
Sadek, Kamal Usef [2 ]
机构
[1] South Valley Univ, Chem Dept, Fac Sci, Qena, AR, Egypt
[2] Menia Univ, Chem Dept, Fac Sci, Al Minya 61519, AR, Egypt
关键词
EFFICIENT GREEN SYNTHESIS; SUPRAMOLECULAR CATALYST; BETA-CYCLODEXTRIN; HIGHLY EFFICIENT; DERIVATIVES; PHTHALAZINE; ACID;
D O I
10.1002/jhet.3659
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple green and efficient one-pot multi-component synthesis of 1H-pyrozolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-triones has been developed utilizing one-pot multi-component reaction of aromatic aldehydes, active methylene reagents, phthalic anhydride, and hydrazine hydrate or alternatively phthalhydrazide in glycerol without catalyst under controlled microwave heating. The current synthetic protocol offers several advantages such as excellent yields, high EcoScale and atom economy, simple working up reactants and products, and the absence of hazardous catalysts or solvents.
引用
收藏
页码:2796 / 2803
页数:8
相关论文
共 42 条
[1]   Synthesis of New [1,2,4]Triazolo[1,5-a]pyrimidine Derivatives: Reactivity of 3-Amino[1,2,4]triazole towards Enaminonitriles and Enaminones [J].
Alnajjar, Abdulaziz ;
Abdelkhalik, Mervat Mohammed ;
Raslan, Mohamed Abdelmonem ;
Ibraheem, Solwan Maher ;
Sadek, Kamal Usef .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (07) :1804-1808
[2]   Magnetic nanoparticles Fe3O4-supported guanidine as an efficient nanocatalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions [J].
Atashkar, Bahareh ;
Rostami, Amin ;
Gholami, Hoshyar ;
Tahmasbi, Bahman .
RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (06) :3675-3681
[3]   3-phenyl-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-α]phthalazines and analogues:: High-affinity γ-aminobutyric acid-A benzodiazepine receptor ligands with α2, α3, and α5-subtype binding selectivity over α1 [J].
Carling, RW ;
Moore, KW ;
Street, LJ ;
Wild, D ;
Isted, C ;
Leeson, PD ;
Thomas, S ;
O'Connor, D ;
McKernan, RM ;
Quirk, K ;
Cook, SM ;
Atack, JR ;
Wafford, KA ;
Thompson, SA ;
Dawson, GR ;
Ferris, P ;
Castro, JL .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (07) :1807-1822
[4]   β-Cyclodextrin as a supramolecular catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives in water and their antimicrobial activities [J].
Chate, Asha V. ;
Bhadke, Priyanka K. ;
Khande, Manisha A. ;
Sangshetti, Jaiprakash N. ;
Gill, Charansingh H. .
CHINESE CHEMICAL LETTERS, 2017, 28 (07) :1577-1582
[5]   Synthesis and optical properties of a series of pyrrolopyridazine derivatives: deep blue organic luminophors for electroluminescent devices [J].
Cheng, Y ;
Ma, B ;
Wudl, F .
JOURNAL OF MATERIALS CHEMISTRY, 1999, 9 (09) :2183-2188
[6]  
Curpenter R. D., 2007, ORG CHEM, V72, P284
[7]   Vasorelaxant activity of phthalazinones and related compounds [J].
del Olmo, E ;
Barboza, B ;
Ybarra, MI ;
López-Pérez, JL ;
Carrón, R ;
Sevilla, MA ;
Boselli, C ;
Feliciano, AS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (10) :2786-2790
[8]   Recent Advances in the Use of Glycerol as Green Solvent for Synthetic Organic Chemistry [J].
Diaz-Alvarez, Alba E. ;
Francos, Javier ;
Crochet, Pascale ;
Cadierno, Victorio .
CURRENT GREEN CHEMISTRY, 2014, 1 (01) :51-65
[9]   Microwave assisted one-pot green synthesis of cinnoline derivatives inside natural sporopollenin microcapsules [J].
Dyab, Amro K. F. ;
Sadek, Kamal Usef .
RSC ADVANCES, 2018, 8 (41) :23241-23251
[10]   One-pot synthesis of multisubstituted imidazoles catalyzed by Dendrimer-PWAn nanoparticles under solvent-free conditions and ultrasonic irradiation [J].
Esmaeilpour, Mohsen ;
Javidi, Jaber ;
Dehghani, Farzaneh ;
Zahmatkesh, Saeed .
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (01) :163-185