An eco-friendly three-component regio- and stereoselective synthesis of highly functionalized dihydroindeno[1,2-b]pyrroles under grinding

作者: Sivasubramanian Muthusaravanan , Chinnathambi Sasikumar , Balasubramanian Devi Bala , Subbu Perumal

DOI: 10.1039/C3GC42150C

关键词:

摘要: Facile three-component domino reactions of (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones with anilines and ninhydrin in an equimolar ratio upon grinding the presence acetic acid (0.1 ml per mmol reactants) afforded highly functionalized dihydroindeno[1,2-b]pyrroles regio- stereoselectively good yields. This protocol has advantages such as solvent-free under grinding, ambient temperature, short reaction times, simple work-up avoiding chromatographic purification excellent

参考文章(67)
Claudia Reidlinger, Renate Dworczak, Hans Junek, Cyanoacetophenone as a Synthon for 1,4,5-Substituted Pyrazoles Monatshefte Fur Chemie. ,vol. 129, pp. 1207- 1211 ,(1998) , 10.1007/PL00010132
James E. Foster, Jesse M. Nicholson, Raymond Butcher, James P. Stables, Ivan O. Edafiogho, Angela M. Goodwin, Michael C. Henson, Carlynn A. Smith, K.R. Scott, Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants. Bioorganic & Medicinal Chemistry. ,vol. 7, pp. 2415- 2425 ,(1999) , 10.1016/S0968-0896(99)00185-6
Yunyun Liu, Rihui Zhou, Jie-Ping Wan, Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions Synthetic Communications. ,vol. 43, pp. 2475- 2483 ,(2013) , 10.1080/00397911.2012.715712
Pitchaimani Prasanna, Kamaraj Balamurugan, Subbu Perumal, J. Carlos Menéndez, A facile, three-component domino protocol for the microwave-assisted synthesis of functionalized naphtho[2,3-b]furan-4,9-diones in water Green Chemistry. ,vol. 13, pp. 2123- 2129 ,(2011) , 10.1039/C0GC00952K
J. S. KAHAN, F. M. KAHAN, R. GOEGELMAN, S. A. CURRIE, M. JACKSON, E. O. STAPLEY, T. W. MILLER, A. K. MILLER, D. HENDLIN, S. MOCHALES, S. HERNANDEZ, H. B. WOODRUFF, J. BIRNBAUM, Thienamycin, a new beta-lactam antibiotic. I. Discovery, taxonomy, isolation and physical properties. The Journal of Antibiotics. ,vol. 32, pp. 1- 12 ,(1979) , 10.7164/ANTIBIOTICS.32.1
Maria Laura Bolognesi, Manuela Bartolini, Andrea Cavalli, Vincenza Andrisano, Michela Rosini, Anna Minarini, Carlo Melchiorre, Design, synthesis, and biological evaluation of conformationally restricted rivastigmine analogues. Journal of Medicinal Chemistry. ,vol. 47, pp. 5945- 5952 ,(2004) , 10.1021/JM049782N
Carl J. Lovely, Hossen Mahmud, An approach to the pyrroloquinoline core of martinelline and martinellic acid Tetrahedron Letters. ,vol. 40, pp. 2079- 2082 ,(1999) , 10.1016/S0040-4039(99)00150-1
Ivan O. Edafiogho, Kethireddy V.V. Ananthalakshmi, Samuel B. Kombian, Anticonvulsant evaluation and mechanism of action of benzylamino enaminones. Bioorganic & Medicinal Chemistry. ,vol. 14, pp. 5266- 5272 ,(2006) , 10.1016/J.BMC.2006.03.049