Synthesis of pyran annulated heterocyclic scaffolds: a highly convenient protocol using dimethylamine
作者： Rathinam Ramesh , Appaswami Lalitha
DOI: 10.1007/S11164-014-1873-5
关键词:
摘要: A facile and rapid three-component synthesis of pharmaceutically diverse pyran annulated heterocycles has been developed via a one-pot condensation aromatic aldehydes, malononitrile, different enolizable C–H-activated acidic compounds in the presence dimethylamine as newer effective organo-catalyst ethanol under mild reaction conditions. Selectivity various derivatives depends on structure enolates. The present protocol synthetic advantages excellent yields much shorter times with no chromatography.
springer.com
sci-hub.se 参考文章(31)
Bernard Pirotte, Jeanine Fontaine, Philippe Lebrun, Recent advances in the chemistry of potassium channel openers Current Medicinal Chemistry. ,vol. 2, pp. 573- 582 ,(1995)
James R. Empfield, Keith Russell, Chapter 9. Potassium Channel Openers Annual Reports in Medicinal Chemistry. ,vol. 30, pp. 81- 90 ,(1995) , 10.1016/S0065-7743(08)60922-7
D. M. Pore, K. A. Undale, B. B. Dongare, U. V. Desai, Potassium Phosphate Catalyzed a Rapid Three-Component Synthesis of Tetrahydrobenzo[b]pyran at Ambient Temperature Catalysis Letters. ,vol. 132, pp. 104- 108 ,(2009) , 10.1007/S10562-009-0074-0
William Kemnitzer, John Drewe, Songchun Jiang, Hong Zhang, Yan Wang, Jianghong Zhao, Shaojuan Jia, John Herich, Denis Labreque, Richard Storer, Karen Meerovitch, David Bouffard, Rabindra Rej, Real Denis, Charles Blais, Serge Lamothe, Giorgio Attardo, Henriette Gourdeau, Ben Tseng, Shailaja Kasibhatla, Sui Xiong Cai, Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 1. Structure-activity relationships of the 4-aryl group. Journal of Medicinal Chemistry. ,vol. 47, pp. 6299- 6310 ,(2004) , 10.1021/JM049640T
Jitender M. Khurana, Bhaskara Nand, Pooja Saluja, DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium Tetrahedron. ,vol. 66, pp. 5637- 5641 ,(2010) , 10.1016/J.TET.2010.05.082
Abu T. Khan, Mohan Lal, Shahzad Ali, Md. Musawwer Khan, One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst Tetrahedron Letters. ,vol. 52, pp. 5327- 5332 ,(2011) , 10.1016/J.TETLET.2011.08.019
Saeed Balalaie, Sorour Ramezanpour, Morteza Bararjanian, Jürgen H. Gross, DABCO‐Catalyzed Efficient Synthesis of Naphthopyran Derivatives via One‐Pot Three‐Component Condensation Reaction at Room Temperature Synthetic Communications. ,vol. 38, pp. 1078- 1089 ,(2008) , 10.1080/00397910701862865
Dalip Kumar, V. Buchi Reddy, Shashwat Sharad, Urvashi Dube, Suman Kapur, A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. European Journal of Medicinal Chemistry. ,vol. 44, pp. 3805- 3809 ,(2009) , 10.1016/J.EJMECH.2009.04.017
Abolghasem Davoodnia, Sadegh Allameh, Samineh Fazli, Niloofar Tavakoli-Hoseini, 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 Chemical Papers. ,vol. 65, pp. 714- 720 ,(2011) , 10.2478/S11696-011-0064-8
Nazario Martín, Angeles Martínez-Grau, Carlos Seoane, José L. Marco, Armando Albert, Félix H. Cano, Michael Addition of Malononitrile to α-Acetylcinnamamides Liebigs Annalen der Chemie. ,vol. 1993, pp. 801- 804 ,(1993) , 10.1002/JLAC.1993199301125