Nano-cellulose-OSnCl4-x: Green and natural-based renewable nanocatalyst for one-pot synthesis of 2-amino-3-phenylsulfonyl-4H-pyran derivatives

被引：0
作者：
Shafe-Mehrabadi, Sayed Rasul [1 ]
Sadeghi, Bahareh [2 ]
Mosslemin, Mohammad Hossein [1 ]
Hashemian, Saeedeh [1 ]
机构：
[1] Islamic Azad Univ, Dept Chem, Yazd Branch, Yazd, Iran
[2] Islamic Azad Univ, Dept Chem, Cent Tehran Branch, Tehran, Iran
来源：
IRANIAN JOURNAL OF CATALYSIS | 2022年 / 12卷 / 04期
关键词：
Phenylsulfonylacetonitrile; pyran derivatives; dimedone; green chemistry; nano-cellulose-OSnCl4-x; MULTICOMPONENT SYNTHESIS; CATALYST; 4-HYDROXYCOUMARIN;
D O I：
10.30495/IJC.2022.1958448.1933
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A highly efficient, eco-friendly procedure has been proposed for the synthesis of 2-amino-3-phenylsulfonyl-4H-pyran derivatives via nano-cellulose-OSnCl4-x catalyst prepared from cotton as support treated with tin tetrachloride (SnCl4). This catalyst is characterized by FT-IR, FESEM, TEM, TGA, and EDX. The TEM results confirmed the size of the nano-cellulose-OSnCl4-x catalyst was below 30 nm. The efficiency of this solid acid catalyst was investigated in one-pot, three-component condensation reactions with aromatic aldehydes, dimedone, and phenylsulfonylacetonitrile under reflux conditions. As a result, 2-amino-3-phenylsulfonyl-4H-pyran derivatives were produced under facile conditions in high yield (84-95%) and high rate (30-50 min) using nano-cellulose-OSnCl4-x as a recyclable catalyst.
引用
收藏
页码：407 / 416
页数：10
相关论文
共 27 条
[1]   Synthesis of Novel 2-Amino-7-Methyl-4-Aryl-3-(Phenylsulfonyl)Pyrano[4,3-b]Pyran-5(4H)-One Derivatives in the Presence TiCl4 Supported on Kaolin as a Nano Catalyst [J].
Abyar, Elahe ;
Sadeghi, Bahareh ;
Mosslemin, Mohammad Hossein .
POLYCYCLIC AROMATIC COMPOUNDS, 2021, 41 (05) :920-928
[2]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[3]   TiCl4/nano Sawdust as a Biocatalyst for the Synthesis of Ethyl 2-Amino-5-Oxo-4H,5H-Pyrano[4,3-b]Pyran-3-Carboxylates [J].
Ashkzari, Abbas Dehghani ;
Sadeghi, Bahareh ;
Zavar, Saleheh .
POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (04) :954-959
[4]   4-hydroxycoumarin in heterocyclic synthesis -: Part III.: Synthesis of some new pyrano[2,3-d]pyrimidine, 2-substituted[1,2,4]triazolo[1,5-c]pyrimidine and pyrimido[1,6-b][1,2,4]triazine derivatives [J].
Bedair, AH ;
El-Hady, NA ;
Abd El-Latif, MS ;
Fakery, AH ;
El-Agrody, AM .
FARMACO, 2000, 55 (11-12) :708-714
[5]   Multicomponent synthesis of 2-imidazolines [J].
Bon, RS ;
van Vliet, B ;
Sprenkels, NE ;
Schmitz, RF ;
de Kanter, FJJ ;
Stevens, CV ;
Swart, M ;
Bickelhaupt, FM ;
Groen, MB ;
Orru, RVA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3542-3553
[6]   Green Nano-Silica Sulfuric Acid-Catalyzed Synthesis of New 6-Amino-8-aryl-7-(benzenesulfonyl)-2-(hydroxymethyl)-pyrano[3,2-b]pyran-4(8H)-one Derivatives [J].
Dehghanpoor, S. ;
Sadeghi, B. ;
Mosslemin, M. H. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (12) :1957-1960
[7]   Basic ionic liquid HEAA catalysed one-pot synthesis of novel 2-amino-3-phenylsulfonyl-4H-pyrans derivatives [J].
Ding, Maohua ;
Zhang, Lei ;
Guo, Hongyun ;
Zhong, Mingqiang .
JOURNAL OF CHEMICAL RESEARCH, 2013, (12) :780-782
[8]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[9]  
El-Agrody Ahmed M., 2000, Acta Pharmaceutica (Zagreb), V50, P111
[10]   Heteroaromatization with 4-hydroxycoumarin part II: Synthesis of some new pyrano[2,3-d] pyrimidines, [1,2,4]triazolo[1,5-c]pyrimidines and pyrimido[1,6-b][1,2,4]triazine derivatives. [J].
El-Agrody, AM ;
El-Latif, MSA ;
El-Hady, NA ;
Fakery, AH ;
Bedair, AH .
MOLECULES, 2001, 6 (06) :519-527
123