Novel Synthetic Route to Fluorinated β‐Carbolines by One‐Pot Reaction

References

• Hino , T. and Nakagawa , M. 1994 . Synthesis of bioacetive nitrogen heterocycles from marine organisms . J. Hetercycl. Chem. , 31 : 625 – 630 .
   Google Scholar
• Magnier , E. and Langlois , Y. 1998 . Manzamine alkaloids, syntheses and synthetic approaches . Tetrahedron. , 54 ( 23 ) : 6201 – 6258 .
   Google Scholar
• Nakagawa , M. 2000 . Enantioselective total synthesis of marine alkaloids, manzamine A and related compounds . J. Hetercycl. Chem. , 37 : 567 – 581 .
   Google Scholar
• Guzman , F. , Cain , M. , Larscheid , P. , Hagen , T. , Cook , J. M. , Schweri , M. , Skolnick , P. and Paul , S. M. 1984 . Biomimetic approach to potential benzodiazepine receptor agonists and antagonists . J. Med. Chem. , 27 ( 5 ) : 564 – 570 .
   PubMedGoogle Scholar
• Dorey , G. , Poissonnet , G. , Potier , M.‐C. , Prado de Carvalho , L. , Venault , P. , Chapouthier , G. , Rossier , J. , Potier , P. and Dodd , R. H. 1989 . Synthesis and benzodiazepine receptor affinities of rigid analogs of 3‐carboxy‐beta‐cabolines: demonstration that the benzodiazepine receptor recognizers preferentially the s‐cis conformation of the 3‐carboxy group . J. Med. Chem. , 32 ( 8 ) : 1799 – 1804 .
   PubMedGoogle Scholar
• Cox , E. D. and Cook , J. M. 1995 . The Pictet‐Spengler condensation: A new direction for an old reaction . Chem. Rev. , 95 ( 6 ) : 1797 – 1842 .
   Google Scholar
• Erickson , W. R. and Gould , S. J. 1985 . Streptonigrin biosynthesis.7.Incorporation of oxygen from oxygen‐18: Evidence for an oxidative.beta.‐carboline cleavage . J. Am. Chem. Soc. , 107 ( 20 ) : 5831 – 5832 .
   Google Scholar
• Boger , D. L. , Yasuda , M. , Mitscher , L. A. , Drake , S. D. , Kitos , P. A. and Thompson , S. C. 1987 . Streptonigrin and lavendamycin partial structures. Probes for the minimum, potent pharmacophore of streptonigrin, lavendamycin and synthetic quinoline‐5, 8‐diones . J. Med. Chem. , 30 ( 10 ) : 1918 – 1928 .
   PubMedGoogle Scholar
• Sandrin , J. , Hollinshead , S. P. and Cook , J. M. 1989 . Pictet‐Spengle reactions in aprotic media. Stereospecificity in the Pictet‐Spengler reaction . J. Org. Chem. , 54 ( 23 ) : 5636 – 5640 .
   Google Scholar
• Kuehne , M. E. and Muth , R. S. 1991 . Total syntheses of yohimbe alkaloids, with stereoselection for the normal, allo, and 3‐epiallo series, based on annelations of 4‐methoxy 1,2‐dihydropyridones . J. Org. Chem. , 56 ( 8 ) : 2701 – 2712 .
   Web of Science ®Google Scholar
• Jiang , W. Q. , Wen , R. and Laroze , J. Y. 1999 . β‐carbolines. 1. Synthesis of Several New Bis‐β‐carboline Compounds . J. Chin. Pharm. Sci. , 8 ( 3 ) : 177 – 179 .
   Google Scholar
• Molina , P. , Murcia , F. and Fresneda , P. M. 1994 . A straightforward and practical formal synthesis of lavendamycin ethyl ester . Tetrahedron Lett. , 35 ( 9 ) : 1453 – 1456 .
   Google Scholar
• Boger , D. L. , Duff , S. R. , Panek , J. S. and Yasuda , M. 1985 . Total synthesis of lavendamycin methyl ester . J. Org. Chem. , 50 ( 26 ) : 5790 – 5795 .
   Google Scholar
• Agnusdei , M. , Bandini , M. , Melloni , A. and Umani‐Ronchi , A. 2003 . New versatile route to the synthesis of tetrahydro‐β‐carbolines and tetrahydro‐pyrano[3,4‐b]indoles via an intramolecular Michael addition catalyzed by InBr3 . J. Org. Chem. , 68 ( 18 ) : 7126 – 7129 .
   PubMedGoogle Scholar
• Kanekiyo , N. , Kuwada , T. , Choshi , T. , Nobuhiro , J. and Hibino , S. 2001 . Total synthesis of β‐carboline Alkaloids, (R)‐(−)‐Pyridindolol Kl, (R)‐(−)‐Pyridindolol K2, and (R)‐(−)‐Pyridindolol . J. Org. Chem. , 66 ( 26 ) : 8793 – 8798 .
   PubMedGoogle Scholar
• Schlecker , W. , Huth , A. , Ottow , E. and Mulzer , J. 1995 . Synthesis of 4‐arylpyridines and substituted β‐carbolines via 1, 4‐Grignard‐Addition to pyridinecarboxamides . Tetrahedron , 51 ( 35 ) : 9531 – 9542 .
   Google Scholar
• Iwaki , T. , Yasuhara , A. and Sakamoto , T. 1999 . Novel synthetic strategy of carbolines via palladium‐catalyzed amination and arylation reaction . J. Chem. Soc., Perkin Trans. , 1 ( 11 ) : 1505 – 1510 .
   Google Scholar
• Zhang , H. and Larock , R. C. 2002 . Synthesis of β‐ and γ‐Carbolines by the palladium/copper‐catalyzed coupling and cyclization of terminal acetylenes . J. Org. Chem. , 67 ( 20 ) : 7048 – 7056 .
   PubMedGoogle Scholar
• Uneyama , K. 1999 . Chemistries of trifluoroacetimidoyl halides: Preparation, reaction, and applications for the synthesis of fluorinated heterocycles . J. Fluorine Chem. , 97 ( 1 ) : 11 – 25 .
   Google Scholar
• Maki , Y. , Kimoto , H. , Fujhii , S. , Nishida , M. and Cohen , L. A. 1989 . Synthesis of 1‐trifluoromethyl‐β‐carboline derivatives . J. Fluorine Chem. , 43 ( 2 ) : 189 – 205 .
   Google Scholar
• Tamura , K. , Mizukami , H. , Maeda , K. , Watanabe , H. and Uneyama , K. 1993 . One‐pot synthesis of trifluoroacetimidoyl halides . J. Org. Chem. , 58 ( 1 ) : 32 – 35 .
   Google Scholar