[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/jkcs.2011.55.4.662

Silica Gel Promoted Mild, Efficient and Inexpensive Protocol for the Preparation of 3,4-dihydropyrano[c]chromenes

Prasanna, T.S.R. (Synthetic Polymer Laboratory, Department of Polymer Science & Tech. Sri Krisnadevaraya University)
Raju, K. Mohana (Synthetic Polymer Laboratory, Department of Polymer Science & Tech. Sri Krisnadevaraya University)

Publication Information

Journal of the Korean Chemical Society / v.55, no.4, 2011 , pp. 662-665 More about this Journal

Abstract

Highly efficient, three-component condensation of aromatic aldehyde, malononitrile and 4-hydroxycoumarin promoted by neat silica gel at room temperature is described. The method offers an excellent alternative to the synthesis of 3,4-dihydropyrano[c]chromenes. The reactions are fast and clean, and the products are obtained with good yield and purity.

Keywords

Silica gel; one pot three-component condensation; aromatic aldehyde; malononitrile; 4-hydroxycoumarin;

Citations & Related Records

Times Cited By SCOPUS : 0

Reference

1	Zhu, J., Bienayme, H., Eds.; Wiley-VCH: Weinheim, 2005
2	Kappe, C. O. Acc. Chem. Res. 2000, 33, 879. DOI
3	Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
4	Ugi, I.; Domling, A.; Werner, B. J. Heteroclcl. Chem. 2000, 37, 647 DOI
5	Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. DOI
6	Shestopalov, A. M.; Emeliyanova,Y. M.; Shestiopolov, A. A.; Rodinovskaya, I. A.; Niazimbetova, A. I.; Evans, D. H. Org. Lett. 2002, 4, 423 DOI
7	Bagley, M. C.; Cale, J. W.; Bower, J. Chem. Commun. 2002, 1682
8	Dallinger, D.; Gorobets, N. Y.; Kappe, C. O. Org. Lett. 2003, 5, 1205. DOI
9	Bonsignore, L.; Loy, G.; Secci, D.; Calignano, A. Eur. J. Med. Chem. 1993, 28, 517. DOI
10	Konkoy, C. S.; Fick, D. B.; Cai, S. X.; Lan, N. C.; Keana, J. F. W. PCT Int Appl WO 0075123 (2000)
11	Khurana, J. M.; Kumar, S. Tetrabutylammonium bromide (TBAB): conditions. Tetrahedron lett. 2009, 50, 4125. DOI
12	Chem. Abstr. 2001, 134, 29313a.
13	Abdolmohammadi, S.; Balalaie, S. Tetrahedron lett. 2007, 48, 3299. DOI
14	Heravi, M. M.; Jani, B. A.; Derikvand, F.; Bamoharram, F. F.; Oskooie, H. A. Catal. Commun. 2008, 10, 272. DOI
15	Kidwai, M. Saxena, S. Synth. Commun. 2006, 36, 2737. DOI
16	Shaker, R. M. Pharmazie. 1996, 51, 148.
17	Wipf, P.; Aoyama, Y.; Benedum, T. E. Org Lett. 2004, 6(20), 3593 DOI
18	You, L.; Feng, S.; An, R.; Wang, X.; Bai, D. Tetrahedron lett. 2008, 49, 5147 DOI
19	Ahmadi, E.; Ramazani, A.; Haghighi, M. N. Tetrahedron Lett. 2007, 48, 6954. DOI

Reference

	Hamzeh Kiyani. (2017) Research on Chemical Intermediates Aqua one-pot, three-component synthesis of dihydropyrano[3,2-c]chromenes and amino-benzochromenes catalyzed by sodium malonate /
7	Ghodsi Mohammadi Ziarani. (2013) HETEROCYCLES Recent Application of 4-Hydroxycoumarin in Multi-Component Reactions / 87 (7) , 1415
10	Hamzeh Kiyani. (2015) Research on Chemical Intermediates Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water / 41 (10) , 7847
2	Abbas Ali Jafari. (2016) Environmental Chemistry Letters High yield room temperature synthesis of pyranochromenes in neutral cetyltrimethylammonium bromide micellar media / 14 (2) , 215
6	Hamzeh Kiyani. (2015) Research on Chemical Intermediates Potassium phthalimide: an efficient and simple organocatalyst for the one-pot synthesis of dihydropyrano[3,2-c]chromenes in aqueous media / 41 (6) , 4031
	Moaz M. Abdou. (2019) Arabian Journal of Chemistry Recent advances in 4-hydroxycoumarin chemistry. Part 2: Scaffolds for heterocycle molecular diversity /
4	(2011) Polycyclic aromatic compounds Copper Oxide Nanoparticles Supported on Ionic Liquid-Modified Magnetic Nanoparticles: A Novel Magnetically Recyclable Catalyst for the Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives / 40 (4) , 1084
1	(2018) Australian journal of chemistry Nanofibre Sepiolite Catalyzed Green and Rapid Synthesis of 2-Amino-4H-chromene Derivatives / 71 (1) , 32
2	(2019) Current organic synthesis Synthesis of 3,4-Dihydropyrano[c]chromenes Using Carbon Microsphere Supported Copper Nanoparticles (Cu-NP/C) Prepared from Loaded Cation Exchange Resin as a Catalyst / 16 (2) , 288
9	(2011) Research on chemical intermediates Amine modified nanozeolites for the three component synthesis of chromenes / 45 (9) , 4693
6	(2020) Organic preparations and procedures international Synthesis of Pyran Annulated Heterocyclic Compounds under Catalyst Free Conditions Using Aqueous Ethylene Glycol / 52 (6) , 564
1	(2011) Polycyclic aromatic compounds Melamine: An Efficient Promoter for Some of the Multi-component Reactions / 41 (1) , 73
10	(2011) Polycyclic aromatic compounds Application of Phosphate Fertilizer Modified by Zinc as a Reusable Efficient Heterogeneous Catalyst for the Synthesis of Biscoumarins and Dihydropyrano[3,2-c]Chromene-3-Carbonitriles under Green Condi / 41 (10) , 2083

KSCI

Silica Gel Promoted Mild, Efficient and Inexpensive Protocol for the Preparation of 3,4-dihydropyrano[c]chromenes Silica Gel을 이용한 효율적인 3,4-dihydropyrano[c]chromenes의 합성

Silica Gel Promoted Mild, Efficient and Inexpensive Protocol for the Preparation of 3,4-dihydropyrano[c]chromenes