Highly efficient green synthesis of the photochromic spironaphthoxazines using an eco-friendly choline hydroxide catalyst

被引:9
作者
Vajekar, Shailesh N. [1 ]
Shankarling, Ganapati S. [1 ]
机构
[1] Inst Chem Technol, Dept Dyestuff Technol, Mumbai 400019, Maharashtra, India
关键词
Choline hydroxide; biodegradable; recyclable; spironaphthoxazines; ONE-POT SYNTHESIS; IONIC LIQUID; SPIROOXAZINES; SPIROPYRANS; ACID; OXIDATION; ALDEHYDES;
D O I
10.1080/00397911.2019.1694690
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A greener route for the synthesis of the photochromic spironaphthoxazines employing a highly efficient, biodegradable and recyclable choline hydroxide catalyst in an aqueous medium has been described. This methodology offers diverse advantages such as mild reaction conditions, short reaction time (1 h), excellent yields (up to 91%), and operational simplicity that make it a useful and attractive option for the synthesis of the spironaphthoxazines. The choline hydroxide showed excellent catalytic performance until five recycles without significant loss of activity. The structures of synthesized spironaphthoxazines were deduced by their H-1 NMR spectra and melting points.
引用
收藏
页码:338 / 347
页数:10
相关论文
共 28 条
[1]   Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions [J].
Abelló, S ;
Medina, F ;
Rodríguez, X ;
Cesteros, Y ;
Salagre, P ;
Sueiras, JE ;
Tichit, D ;
Coq, B .
CHEMICAL COMMUNICATIONS, 2004, (09) :1096-1097
[2]   Biodegradable choline hydroxide promoted environmentally benign thiolysis of epoxides [J].
Azizi, Najmedin ;
Edrisi, Mahtab .
TETRAHEDRON LETTERS, 2016, 57 (05) :525-528
[3]   Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines [J].
Balmond, Edward I. ;
Tautges, Brandon K. ;
Faulkner, Andrea L. ;
Or, Victor W. ;
Hodur, Blanka M. ;
Shaw, Jared T. ;
Louie, Angelique Y. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :8744-8758
[4]   Spiropyrans and spirooxazines for memories and switches [J].
Berkovic, G ;
Krongauz, V ;
Weiss, V .
CHEMICAL REVIEWS, 2000, 100 (05) :1741-1753
[5]   Industrial organic photochromic dyes [J].
Corns, S. Nigel ;
Partington, Steven M. ;
Towns, Andrew D. .
COLORATION TECHNOLOGY, 2009, 125 (05) :249-261
[6]   Transformation of 6'-aminosubstituted spironaphthoxazines induced by Pb(II) and Eu(III) cations [J].
Fedorova, OA ;
Koshkin, AV ;
Gromov, SP ;
Strokach, YP ;
Valova, TM ;
Alfimov, MV ;
Feofanov, AV ;
Alaverdian, IS ;
Lokshin, VA ;
Samat, A .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (06) :504-512
[7]   Concentrated solar radiation aided energy efficient protocol for oxidation of alcohol using biodegradable task specific ionic liquid-choline peroxydisulfate [J].
Gadilohar, Balu L. ;
Deshpande, Saurabh S. ;
Pinjari, Dipak V. ;
Shankarling, Ganapati S. .
SOLAR ENERGY, 2016, 139 :328-336
[8]   Chemical stability of choline-based ionic liquids supported on carbon materials [J].
Garcia-Suarez, Eduardo J. ;
Menendez-Vazquez, Carmen ;
Garcia, Ana B. .
JOURNAL OF MOLECULAR LIQUIDS, 2012, 169 :37-42
[9]   Metal-free oxidation of aldehydes to acids using the 4Na2SO4•2H2O2•NaCl adduct [J].
Gayakwad, Eknath M. ;
Patil, Vilas V. ;
Shankarling, Ganapati S. .
ENVIRONMENTAL CHEMISTRY LETTERS, 2017, 15 (03) :459-465
[10]   Amberlyst-15 catalysed oxidative esterification of aldehydes using a H2O2 trapped oxidant as a terminal oxidant [J].
Gayakwad, Eknath M. ;
Patil, Vilas V. ;
Shankarling, Ganapati S. .
NEW JOURNAL OF CHEMISTRY, 2017, 41 (07) :2695-2701