A green synthesis of 1,7-dihydrodipyrazolo[3,4-b:4',3'-e]pyridin-3(2H)-one derivatives from deamination cyclization reactions in aqueous medium

被引:6
作者
Xu, Hui [1 ]
Li, Lei [1 ]
Wang, Zhansheng [1 ]
Xi, Junhua [1 ]
Rong, Liangce [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Pyrazolo[3,4-b:4 ',3 '-e]pyridine; Green synthesis; Deamination reaction; Aqueous medium; 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one; BIOLOGICAL EVALUATION; PYRAZOLOPYRIDINE DERIVATIVES; ONE-POT; WATER; EFFICIENT; INHIBITORS; ANTAGONISTS; ACTIVATION; SYSTEMS; FACILE;
D O I
10.1007/s11164-018-3302-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Efficient and green reactions of different aromatic aldehydes, 3-amino-1-phenyl-1H-pyrazol-5(4H)-one, and substituted 3-aminopyrazoles for the synthesis of pyrazolo[3,4-b:4',3'-e]pyridin-3(2H)-one derivatives have been reported through deamination cyclization reactions. This is a new route for the generation of pyrazolo[3,4-b:4',3'-e]pyridin-3(2H)-one compounds. According to the reported literature, these kinds of compounds have important optical properties, and have potential application prospects. Other advantages of this process are simple operation, easy separation, and a wide range of substrates. Best of all, this method possesses an environmentally benign procedure.
引用
收藏
页码:3211 / 3226
页数:16
相关论文
共 34 条
[1]   Solvent-free microwave-assisted synthesis of novel pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity [J].
Acosta, Paola ;
Insuasty, Braulio ;
Ortiz, Alejandro ;
Abonia, Rodrigo ;
Sortino, Maximiliano ;
Zacchino, Susana A. ;
Quiroga, Jairo .
ARABIAN JOURNAL OF CHEMISTRY, 2016, 9 (03) :481-492
[2]   Design, synthesis, and biological evaluation of AT1 angiotensin II receptor antagonists based on the pyrazolo[3,4-b]pyridine and related heteroaromatic bicyclic systems [J].
Cappelli, Andrea ;
Nannicini, Chiara ;
Gallelfi, Andrea ;
Giuliani, Germano ;
Valenti, Salvatore ;
Mohr, Gal la Pericot ;
Anzini, Maurizio ;
Mennuni, Laura ;
Ferrari, Flora ;
Caselli, Gianfranco ;
Giordani, Antonio ;
Peris, Walter ;
Makovec, Francesco ;
Giorgi, Gianluca ;
Vomero, Salvatore .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :2137-2146
[3]   Facile and efficient synthesis of pyrazoloisoquinoline and pyrazolopyridine derivatives using recoverable carbonaceous material as solid acid catalyst [J].
Chen, Zhu ;
Shi, Yingxia ;
Shen, Qingqing ;
Xu, Haixia ;
Zhang, Furen .
TETRAHEDRON LETTERS, 2015, 56 (33) :4749-4752
[4]   On-Water Synthesis of Biaryl Sulfonyl Fluorides [J].
Chinthakindi, Praveen K. ;
Kruger, Hendrik G. ;
Govender, Thavendran ;
Naicker, Tricia ;
Arvidsson, Per I. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06) :2618-2623
[5]   Highly-bright white organic light-emitting diodes based on a single emission layer [J].
Chuen, CH ;
Tao, YT .
APPLIED PHYSICS LETTERS, 2002, 81 (24) :4499-4501
[6]   NHC-Cu(I)-Catalyzed Friedlander-Type Annulation of Fluorinated o-Aminophenones with Alkynes on Water: Competitive Base-Catalyzed Dibenzo[b,f][1,5]diazocine Formation [J].
Czerwinski, Pawel ;
Michalak, Michal .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (15) :7980-7997
[7]   Antileishmanial pyrazolopyridine derivatives: Synthesis and structure-activity relationship analysis [J].
de Mello, H ;
Echevarria, A ;
Bernardino, AM ;
Canto-Cavalheiro, M ;
Leon, LL .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (22) :5427-5432
[8]   Novel One-Pot, Three-Component Synthesis of Spiro[Indoline-pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine]trione Library [J].
Ghahremanzadeh, Ramin ;
Sayyafi, Maryam ;
Ahadi, Somayeh ;
Bazgir, Ayoob .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (03) :393-396
[9]   Structure-activity studies of a series of dipyrazolo[3,4-b:3′,4′-d]pyridin-3-ones binding to the immune regulatory protein B7.1 [J].
Green, NJ ;
Xiang, J ;
Chen, J ;
Chen, LR ;
Davies, AM ;
Erbe, D ;
Tam, S ;
Tobin, JF .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (13) :2991-3013
[10]   Blue electroluminescence of novel pyrazoloquinoline and bispyrazolopyridine derivatives in doped polymer matrices [J].
He, Z ;
Milburn, GHW ;
Danel, A ;
Puchala, A ;
Tomasik, P ;
Rasala, D .
JOURNAL OF MATERIALS CHEMISTRY, 1997, 7 (12) :2323-2325