A facile and one-pot synthesis of new tetrahydrobenzo[b]pyrans in water under microwave irradiation

被引:19
作者
Khumalo, Mandlenkosi Robert [1 ]
Maddila, Surya Narayana [1 ]
Maddila, Suresh [1 ]
Jonnalagadda, Sreekantha B. [1 ]
机构
[1] Univ KwaZulu Natal, Sch Chem & Phys, Westville Campus,Chiltern Hills, ZA-4000 Durban, South Africa
关键词
Microwave irradiation; Multicomponent reactions; One-pot synthesis; Green synthesis; Benzopyrans; GREEN SYNTHESIS; MULTICOMPONENT SYNTHESIS; DERIVATIVES-SYNTHESIS; BIOLOGICAL-ACTIVITY; REUSABLE CATALYST; EFFICIENT;
D O I
10.1186/s13065-019-0651-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Eleven new tetrahydrobenzo[b]pyran derivatives were synthesized via a three component reaction of different aromatic aldehydes, methyl cyanoacetate and 1,3-cyclohexadione, with water as solvent under catalyst-free microwave irradiation. The structures of all the new molecules were well analysed and their structures established by using various spectral techniques (H-1 NMR, C-13 NMR, N-15 NMR and HRMS). Various advantages of reported protocol are the ease of preparation, short reaction times (10 min), aqueous solvent and excellent yields (89-98%). Additionally, this method provides a clean access to the desired products by simple workup.
引用
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页数:7
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共 47 条
[1]   Tetra-methyl ammonium hydroxide:: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media [J].
Balalaie, Saeed ;
Sheikh-Ahmadi, Masoumeh ;
Bararjanian, Morteza .
CATALYSIS COMMUNICATIONS, 2007, 8 (11) :1724-1728
[2]   RuO2/ZrO2 as an efficient reusable catalyst for the facile, green, one-pot synthesis of novel functionalized halopyridine derivatives [J].
Bhaskaruni, Sandeep V. H. S. ;
Maddila, Suresh ;
van Zyl, Werner E. ;
Jonnalagadda, Sreekantha B. .
CATALYSIS COMMUNICATIONS, 2017, 100 :24-28
[3]   One-pot synthesis of 2-amino-3-cyano-4-arylsubstituted tetrahydrobenzo[b]pyrans catalysed by silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst [J].
Davoodnia, Abolghasem ;
Allameh, Sadegh ;
Fazli, Samineh ;
Tavakoli-Hoseini, Niloofar .
CHEMICAL PAPERS, 2011, 65 (05) :714-720
[4]   Synthesis and antimalarial evaluation of novel benzopyrano[4,3-b]benzopyran derivatives [J].
Devakaram, Ruth ;
Black, David StC. ;
Andrews, Katherine T. ;
Fisher, Gillian M. ;
Davis, Rohan A. ;
Kumar, Naresh .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (17) :5199-5206
[5]   A novel multicomponent microwave-assisted synthesis of 5-aza-adenines [J].
Dolzhenko, Anton V. ;
Kalinina, Svetlana A. ;
Kalinin, Dmitrii V. .
RSC ADVANCES, 2013, 3 (36) :15850-15855
[6]   Green Synthesis of Tetrahydrobenzo[b]Pyrans by Microwave Assisted Multi-Component One-Pot Reactions in PEG-400 [J].
Feng, Chun ;
Wang, Qiuyan ;
Lu, Cuifen ;
Yang, Guichun ;
Chen, Zuxing .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2012, 15 (01) :100-103
[7]   Synthesis, Structure, and Properties of New Mg(II)-Metal-Organic Framework and Its Prowess as Catalyst in the Production of 4H-Pyrans [J].
Gangu, Kranthi Kumar ;
Maddila, Suresh ;
Mukkamala, Saratchandra Babu ;
Jonnalagadda, Sreekantha B. .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2017, 56 (11) :2917-2924
[8]   Novel iron doped calcium oxalates as promising heterogeneous catalysts for one-pot multi-component synthesis of pyranopyrazoles [J].
Gangu, Kranthi Kumar ;
Maddila, Suresh ;
Maddila, Surya Narayana ;
Jonnalagadda, Sreekantha B. .
RSC ADVANCES, 2017, 7 (01) :423-432
[9]   Synthesis, Molecular Docking Study and in vitro Anticancer Activity of Tetrazole Linked Benzochromene Derivatives [J].
Gorle, Sridevi ;
Maddila, Suresh ;
Maddila, Surya N. ;
Naicker, Kovashnee ;
Singh, Moganavelli ;
Singh, Parvesh ;
Jonnalagadda, Sreekantha B. .
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2017, 17 (03) :464-470
[10]   Synthesis, Biological Activity of Pyrimidine Linked with Morpholinophenyl Derivatives [J].
Gorle, Sridevi ;
Maddila, Suresh ;
Chokkakula, Santosh ;
Lavanya, Palakondu ;
Singh, Moganavelli ;
Jonnalagadda, Sreekanth B. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (06) :1852-1858