A simple and efficient one-pot synthesis of 2-alkyl/aryl/pyridyl substituted 2H-chromenes
作者： Lenka Chandrasekhara Rao , Nandigama Satish Kumar , Nanubolu Jagadeesh Babu , Harshadas Mitaram Meshram
DOI: 10.1039/C5NJ01377A
关键词:
摘要: A simple and efficient protocol is demonstrated to synthesize medicinally significant new 2-pyridyl/aryl/alkyl substituted 2H-chromenes. The construction of these chromene systems was through a chemoselective Knoevenagel condensation/hemiketalisation process. reaction afforded variety products in good excellent yields. This methodology has potential applications the synthesis biologically relevant molecules. For first time we have synthesized 2-pyridyl/aryl 2H-chromenes one-pot reaction.
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sci-hub.se 参考文章(29)
Corinne Comoy, Christophe Marot, Tchao Podona, Marie-Laure Baudin, Luc Morin-Allory, Gérald Guillaumet, Bruno Pfeiffer, Daniel-Henry Caignard, Pierre Renard, Marie-Claire Rettori, Gérard Adam, Béatrice Guardiola-Lemaître, 3-Amino-3,4-dihydro-2H-1-benzopyran Derivatives as 5-HT1AReceptor Ligands and Potential Anxiolytic Agents. 2. Synthesis and Quantitative Structure−Activity Relationship Studies of Spiro[pyrrolidine- and piperidine-2,3‘(2‘H)-benzopyrans]† Journal of Medicinal Chemistry. ,vol. 39, pp. 4285- 4298 ,(1996) , 10.1021/JM950861W
Fei Liu, Todd Evans, Bhaskar C. Das, Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates Tetrahedron Letters. ,vol. 49, pp. 1578- 1581 ,(2008) , 10.1016/J.TETLET.2008.01.008
Juan Pablo Cueva, Gianfabio Giorgioni, Russell A. Grubbs, Benjamin R. Chemel, Val J. Watts, David E. Nichols, trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist. Journal of Medicinal Chemistry. ,vol. 49, pp. 6848- 6857 ,(2006) , 10.1021/JM0604979
Liliya V. Frolova, Indranil Malik, Pavel Y. Uglinskii, Snezna Rogelj, Alexander Kornienko, Igor V. Magedov, Multicomponent Synthesis of 2,3-Dihydrochromeno[4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones: A Novel Heterocyclic Scaffold with Antibacterial Activity. Tetrahedron Letters. ,vol. 52, pp. 6643- 6645 ,(2011) , 10.1016/J.TETLET.2011.10.012
Pramod B. Thakur, Harshadas M. Meshram, “On water” catalyst-free, column chromatography-free and atom economical protocol for highly diastereoselective synthesis of novel class of 3-substituted, 3-hydroxy-2-oxindole scaffolds at room temperature RSC Advances. ,vol. 4, pp. 5343- 5350 ,(2014) , 10.1039/C3RA46271D
Kathlyn A. Parker, Thomas L. Mindt, Electrocyclic Ring Closure of the Enols of Vinyl Quinones. A2H-Chromene Synthesis Organic Letters. ,vol. 3, pp. 3875- 3878 ,(2001) , 10.1021/OL0167199
Xinbo Wang, Yongbo Zhang, Haibo Tan, Yanchao Wang, Peng Han, David Zhigang Wang, Enantioselective organocatalytic mannich reactions with autocatalysts and their mimics. Journal of Organic Chemistry. ,vol. 75, pp. 2403- 2406 ,(2010) , 10.1021/JO902500B
Jae-Hwan Kwak, Hae-Eun Kang, Jae-Kyung Jung, Hwajung Kim, Jungsook Cho, Heesoon Lee, Synthesis of 7-hydroxy-4-oxo-4H-chromene-and 7-hydroxychroman-2-carboxylic acidN-alkyl amides and their antioxidant activities Archives of Pharmacal Research. ,vol. 29, pp. 728- 734 ,(2006) , 10.1007/BF02973917
Charlotta Mellin, Jerk Vallgaarda, David L. Nelson, Lena Bjoerk, Hong Yu, Nils Erik Anden, Ingeborg Csoeregh, Lars Erik Arvidsson, Uli Hacksell, A 3 dimensional model for 5-HT1A-receptor agonists based on stereoselective methyl-substituted and conformationally restricted analogs of 8-hydroxy-2-(dipropylamino)tetralin Journal of Medicinal Chemistry. ,vol. 34, pp. 497- 510 ,(1991) , 10.1021/JM00106A004
Pramod B. Thakur, Harshadas M. Meshram, “On water” highly atom economical and rapid synthesis of a novel class of 3-hydroxy-2-oxindole scaffolds under a catalyst-free and column chromatography-free protocol at room temperature RSC Advances. ,vol. 4, pp. 6019- 6026 ,(2014) , 10.1039/C3RA46613B