79823-24-8Relevant academic research and scientific papers
Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity
Reyes-Gutierrez, Paul E.,Camacho, Jose R.,Ramirez-Apan, Ma. Teresa,Osornio, Yazmin M.,Martinez, Roberto
experimental part, p. 4374 - 4382 (2010/11/04)
A three-step protocol for the synthesis of 1,2,3,8,9-pentasubstituted-5,6- dihydropyrrolo[2,1-a]isoquinolines is described, using van LeuseN′s polysubstituted pyrrole construction followed by intramolecular radical-oxidative cyclization of the isoquinoline system. The cytotoxic activities of the dihydropyrroloisoquinolines were tested on six tumor cell lines. Preliminary structure-activity studies revealed the importance of the identity of the aromatic substituent at the C-2 position, particularly a phenyl, m-(amino) phenyl or m-(cyclohexylmethylpiperazinamide) phenyl substituent, for cytotoxic activity.
Heterocycles from Nitroalkenes, I. - Pyrroles via Michael Addition of Enamines
Meyer, Horst
, p. 1534 - 1544 (2007/10/02)
The principle of a general pyrrole synthesis via cyclising Michael addition of enamines to nitroalkenes is outlined.Condensation of the nitroalkene 7 with various enamines yields the pyrroles 9, 11, 12, 14, 15, 17, 18, 20, 22, 26, 27, 29, and 31.Reaction of 1-nitro-1,2-diphenylethene and the enamine 8 furnishes the pyrroloisoquinoline 32 while addition of 8 to 1-nitrocyclohexene is followed by ring closure to the indoloisoquinoline 33.The pyrrole 14 can also be prepared by multiple-component syntheses, further examples of which are the syntheses of the pyrroles 35, 36, 37, and 38.Scope and advantages of the presented pyrrole synthesis are discussed.
