Meglumine catalyzed one pot synthesis of new fluorescent 2-amino-4-pyrazolyl-6-aryldiazenyl-4H-chromene-3-carbonitriles

被引:7
作者
Korade, Suyog N. [1 ]
Mhaldar, Pradeep M. [1 ]
Kulkarni, Prafulladatta P. [2 ]
Rashinkar, Gajanan S. [1 ]
Pore, Dattaprasad M. [1 ]
机构
[1] Shivaji Univ, Dept Chem, Kolhapur 416004, Maharashtra, India
[2] Gogate Jogalekar Coll, Dept Chem, Ratnagiri, India
关键词
Diazo compounds; green chemistry; heterocycles; multicomponent reaction; optical properties; THROUGHPUT SCREENING ASSAY; ACTIVE METHYLENE; ANTITUMOR EVALUATION; DERIVATIVES; DISCOVERY; SERIES; 4-ARYL-4H-CHROMENES; SALICYLALDEHYDES; CHEMISTRY; PROBE;
D O I
10.1080/00397911.2021.1934875
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Meglumine, a biodegradable basic organo-catalyst has been efficiently explored for the one-pot synthesis of new fluorescent 2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-6-aryldiazenyl-4H-chromene-3-carbonitriles in an aqueous medium at room temperature. The synthesized compounds were found highly fluorescent when screened for photoluminescence properties. The planar structure equipped with substituted aryldiazenyl group led to the extension of conjugation that facilitated fluorescence emission in the visible region with a large stokes shift of 290-294 nm. The novelty of work is a synthesis of highly conjugated molecular assembly, high yield in shorter reaction time, energy efficiency, atom economy, utilization of water as a universal green solvent and meglumine as an eco-benign organo-catalyst.
引用
收藏
页码:2336 / 2348
页数:13
相关论文
共 42 条
[1]   One-pot synthesis of dithiocarbamates accelerated in water [J].
Azizi, N ;
Aryanasab, F ;
Torkiyan, L ;
Ziyaei, A ;
Saidi, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3634-3635
[2]   SYNTHESIS AND CHEMISTRY OF "7-AMINO-4-(TRIFLUOROMETHYL)COUMARIN AND ITS AMINO-ACID AND PEPTIDE DERIVATIVES [J].
BISSELL, ER ;
MITCHELL, AR ;
SMITH, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (12) :2283-2287
[3]   Determining the geometries of transition states by use of antihydrophohic additives in water [J].
Breslow, R .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (07) :471-478
[4]   Heterocyclization of thioamides containing an active methylene group (review) [J].
Britsun, V. N. ;
Esipenko, A. N. ;
Lozinskii, M. O. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (12) :1429-1459
[5]   The antiseptic properties of the amino derivatives of styryl and anil quinoline. [J].
Browning, CH ;
Cohen, JB ;
Ellingworth, S ;
Gulbransen, R .
PROCEEDINGS OF THE ROYAL SOCIETY OF LONDON SERIES B-CONTAINING PAPERS OF A BIOLOGICAL CHARACTER, 1926, 100 (703) :293-325
[6]  
Child R., 1977, Chem. Abstr., P6031
[7]   Privileged structures: Applications in drug discovery [J].
DeSimone, RW ;
Currie, KS ;
Mitchell, SA ;
Darrow, JW ;
Pippin, DA .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2004, 7 (05) :473-493
[8]   A review of aqueous organic reactions for the undergraduate teaching laboratory [J].
Dicks, Andrew P. .
GREEN CHEMISTRY LETTERS AND REVIEWS, 2009, 2 (01) :9-21
[9]   Catalysis of salicylaldehydes and two different C-H acids with electricity:: First example of an efficient multicomponent approach to the design of functionalized medicinally privileged 2-Amino-4H-Chromene scaffold [J].
Elinson, Michail N. ;
Dorofeev, Alexander S. ;
Miloserdov, Fedor M. ;
Ilovalsky, Alexey I. ;
Feducovich, Sergey K. ;
Belyakov, Pavel A. ;
Nikishin, Gennady I. .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (04) :591-601
[10]   Solvent-free and 'on-water' multicomponent assembling of salicylaldehydes, malononitrile and 3-methyl-2-pyrazolin-5-one: A fast and efficient route to the 2-amino-4-(1H-pyrazol-4-yl)-4H-chromene scaffold [J].
Elinson, Michail N. ;
Nasybullin, Ruslan F. ;
Ryzhkov, Fedor V. ;
Egorov, Mikhail P. .
COMPTES RENDUS CHIMIE, 2014, 17 (05) :437-442