Efficient Synthesis of Pyrrolo[1,2-f]phenanthridine Derivatives via Dipolar Cycloaddition of Phenanthridine, Activated Acetylenes, and Ethyl Bromopyruvate

REFERENCES

• Harayama , T. ; Hori , A. ; Abe , H. ; Takeuchi , Y. Concise synthesis of pyrrolophenanthridine alkaloids using a Pd-mediated biaryl coupling reaction with regioselective C–H activation via the intramolecular coordination of the amine to Pd . Tetrahedron 2004 , 60 , 1611 – 1616 .
   Web of Science ®Google Scholar
• Chattopadhyay , S. C. ; Chattopadhyay , U. ; Marthur , P. P. ; Saini , K. S. ; Ghosal , S. Effects of hippadine, an amaryllidaceae alkaloid, on testicular function in rats . Planta Med. 1983 , 49 , 252 – 254 .
   PubMed Web of Science ®Google Scholar
• Petti , G. R. ; Gaddamidi , V. ; Goswani , A. ; Cragg , G. M. Antineoplastic agents, 99: Amaryllis belladonna . J. Nat. Prod. 1984 , 47 , 796 – 801 .
   PubMed Web of Science ®Google Scholar
• Zee-Cheng , R. K. Y. ; Yan , S.-J. ; Chen , C.-C. Antileukemic activity of ungeremine and related compounds: Preparation of analogs of ungeremine by a practical photochemical reaction . J. Med. Chem. 1978 , 21 , 199 – 203 .
   PubMed Web of Science ®Google Scholar
• Buyanov , V. N. ; Baberkina , E. P. ; Samoilova , M. E. ; Akhvlediani , R. N. ; Frolova , E. P. ; Kurkovskaya , L. N. ; Ershova , Y. A. ; Safonova , T. S. ; Korovin , B. V. ; Suvorov , N. N. Khim.-farm. Zh. 1994 , 28 , 10 – 16 .
   Google Scholar
• Almerico , A. A. ; Mingoia , F. ; Diana , P. ; Barraja , P. ; Montalbano , A. Pyrrolo[1,2-f]phenanthridines and related non-rigid analogues as antiviral agents. Eur. J. Med. Chem. 2002, 37, 3–10.
   PubMed Web of Science ®Google Scholar
• Richmond , C. J. ; Parenty , A. D. C. ; Song , Y.-F. ; Cooke , G. ; Cronin , L. Realization of a “lockable” molecular switch via pH- and redox-modulated cyclization . J. Am. Chem. Soc. 2008 , 130 , 13059 – 13065 .
   PubMed Web of Science ®Google Scholar
• Kitson , P. J. ; Parenty , A. D. C. ; Richmond , C. J. ; Long , D.-L. ; Cronin , L. A new C–C bond-forming annulation reaction leading to pH switchable heterocycles . Chem. Commun. 2009 , 4067 – 4069 .
   PubMed Web of Science ®Google Scholar
• Boekelheide , V. ; Fahrenholtz , K. The formation of pyrrocolines by the reaction of dimethyl acetylenedicarboxylate with heterocyclic zwitterions . J. Am. Chem. Soc. 1961 , 83 , 458 – 462 .
   Web of Science ®Google Scholar
• Padwa , A. ; Austin , D. J. ; Precedo , L. ; Zhi , L. Cycloaddition reactions of pyridinium and related azomethine ylides . J. Org. Chem. 1993 , 58 , 1144 – 1150 .
   Web of Science ®Google Scholar
• Yavari , I. ; Hosseinpour , R. ; Pashazadeh , R. ; Skoulika , S. Novel synthesis of functionalized indolizine derivatives from Huisgen's zwitterions and 1-methylimidazole/dichloroketene adduct . Synlett 2012 , 23 , 2103 – 2105 .
   Google Scholar
• Yue , G. ; Wan , Y. ; Song , S. ; Yang , G. ; Chen , Z. Synthesis of a library of benzoindolizines using poly(ethylene glycol) as soluble support . Bioorg. Med. Chem. Lett. 2005 , 15 , 453 – 458 .
   PubMed Web of Science ®Google Scholar
• Kianmehr , E. ; Estiri , H. ; Bahreman , A. Efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a]quinoline derivatives in aqueous media . J. Heterocycl. Chem. 2009 , 46 , 1203 – 1206 .
   Web of Science ®Google Scholar
• Wu , L. ; Sun , J. ; Yan , C. Efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a]quinoline derivatives via one-pot two-step metal-catalyzed three-component reactions . Chin. J. Chem. 2012 , 30 , 590 – 593 .
   Web of Science ®Google Scholar
• Acheson , R. M. ; Plunkett , A. O. Addition reactions of heterocyclic compounds, part XI: The constitution of some adducts from phenanthridine and dimethyl acetylenedicarboxylate . J. Chem. Soc. 1962 , 3758 – 3770 .
   Web of Science ®Google Scholar
• Potacek , M. ; Topinka , T. ; Dostal , J. ; Marek , J. Phenanthridinium-based azomethine ylides in 1,3-dipolar cycloaddition with dimethyl acetylenedicarboxylate . Collect. Czech. Chem. Commun. 1994 , 59 , 2641 – 2649 .
   Web of Science ®Google Scholar
• Yavari , I. ; Hossaini , Z. ; Sabbaghan , M. A synthesis of pyrrolo[2,1-a]isoquinolines through the reaction of activated acetylenes and isoquinoline in the presence of ethyl bromopyruvate . Tetrahedron Lett. 2006 , 47 , 6037 – 6040 .
   Web of Science ®Google Scholar
• Ming , L. ; Zhong-Xuan , Q. ; Li-Rong , W. ; Zhong-Min , Z. Novel regio- and stereo-selectivity: Synthesis of dihydropyrrolo[1,2-f]phenanthridines via isocyanide-based multicomponent reaction . Tetrahedron 2011 , 67 , 3638 – 3648 .
   Web of Science ®Google Scholar
• Mehrabi , H. ; Hatami-pour , M. A synthesis of functionalized pyrido[1,2-f]phenanthridines from phenanthiridine, activated acetylenes, and arylidenemalononitriles . Synth. Commun. 2013 , 43 , 611 – 618 .
   Web of Science ®Google Scholar