First Total Synthesis of (Z)-11-(2-oxopropylidene)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(10H)-one

REFERENCES

• Evans , B. E. ; Rittle , K. E. ; Bock , M. G. ; Dipardo , R. M. ; Freiddinger , R. M. ; Whitter , N. L. ; Lundell , G. F. ; Veber , D. F. ; Anderson , P. S. Methods for drug discovery: Development of potent, selective, orally effective cholecystokinin antagonists . J. Med. Chem. 1988 , 31 , 2235 – 2246 .
   PubMed Web of Science ®Google Scholar
• (a) Carlier , P. R. ; Zhao , H. ; MacQuarrie-Hunter , S. L. ; DeGuzman , J. C. ; Hsu , D. C. Enantioselective synthesis of diversely substituted quaternary 1,4-benzodiazepin-2-ones and 1,4-benzodiazepine-2,5-diones . J. Am. Chem. Soc. 2006 , 128 , 15215 – 15220 ; (b) Ellman , J. A. Design, synthesis, and evaluation of small-molecule libraries . Acc. Chem. Res. 1996 , 29 , 132 – 143 .
   PubMedGoogle Scholar
• Boojamra , C. G. ; Burow , K. M. ; Thompson , L. A. ; Ellman , J. A. Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones: Library preparation and demonstration of synthesis generality . J. Org. Chem. 1997 , 62 , 1240 – 1256 .
   Web of Science ®Google Scholar
• Herpin , T. F. ; Van Kirk , K. G. ; Salvino , J. M. ; Yu , S. T. ; Labaudiniere , R. F. Synthesis of a 10,000 member 1,5-benzodiazepine-2-one library by the directed sorting method . J. Comb. Chem. 2000 , 2 , 513 – 521 .
   PubMedGoogle Scholar
• Wu , Z. ; Ercole , F. ; FitzGerald , M. ; Perera , S. ; Riley , P. ; Campbell , R. ; Pham , Y. ; Rea , P. ; Sandanayake , S. ; Mathieu , M. N. ; Bray , A. M. ; Ede , N. J. Synthesis of tetrahydro-1,4-benzodiazepine-2-ones on hydrophilic polyamide synphase lanterns . J. Comb. Chem. 2003 , 5 , 166 – 171 .
   PubMedGoogle Scholar
• (a) Gregson , J. S. ; Howard , P. W. ; Hartley , J. A. ; Brooks , N. A. ; Adams , L. J. ; Jenkins , T. ; Kellan , L. R. ; Thurston , D. E. Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity. J. Med. Chem. 2001, 44, 737–748; (b) Kamal , A. ; Ramulu , P. ; Srinivas , O. ; Ramesh , G. Synthesis of C-8 methanesulphonate substituted pyrrolobenzodiazepines as potential antitumour agents. Bioorg. Med. Chem. Lett. 2003, 13, 3517–3519; (c) Kamal , A. ; Ramesh , G ; Srinivas , O. ; Ramulu , P. Synthesis and antitumour activity of pyrene-linked pyrrolo [2,1-c] and benzodiazepine hybrids. Bioorg. Med. Chem. Lett. 2004, 14, 471–474; (d) Kamal , A. ; Hari Babu , A. ; Venkata Ramana , A. ; Venkata Ramana , K. ; Vijaya Bharathi , E. ; Shiva Kumar , M. Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines and their conjugates by azido reductive cyclization strategy as potential DNA-binding agents. Bioorg. Med. Chem. Lett. 2005, 15, 2621–2623.
   PubMed Web of Science ®Google Scholar
• Carbateas , P. M. 1,2,3,10,11,11A-Hexahydro-5H-pyrrolo(2,1-C)(1,4)benzodiazepine-5,11-diones. US Patent 3,732,212, 1973; Chem. Abstr. 1973, 79, P42570x; US Patent 3,763,183, 1973; Chem. Abstr. 1973, 79, P146567t; US Patent 3,860,600, 1975; Chem. Abstr. 1975 , 83 , P58892x .
   Google Scholar
• Sterling Drug Inc. (New York, NY). Octahydropyrrido[2,1-c][1,4]benzodiazepines. US Patent 3860600, 1975 .
   Google Scholar
• (a) Wright , W. B. , Jr. ; Pyrrolo-benzodiazepines: Method of preparation and method of use. US Patent 3947408, 1976; (b) Wright , W. B. , Jr. ; Brabander , H. J. ; Greenblatt , E. N. ; Day , I. P. ; Hardy , H. A. , Jr. , Derivatives of 1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzo-diazepine-5,11(10H)-dione as anxiolytic agents . J. Med. Chem. 1978 , 21 , 1087 – 1089 .
   PubMed Web of Science ®Google Scholar
• Nakatani , S. ; Yamamoto , Y. ; Hayashi , M. ; Komiyama , K. ; Ishibashi , M. Cycloanthranilylproline-derived constituents from a myxomycete Fuligo . candida. Chem. Pharm. Bull. 2004 , 52 ( 3 ), 368 – 370.
   PubMed Web of Science ®Google Scholar
• Cledera , P. ; Avendafio , C. ; Menendez , J. C. Rapid analogue synthesis of C-5 substituted 1,2,3-triazolo-[1,5-a]quinazolines . Tetrahedron. 2002 , 58 , 9973 – 9981 .
   Google Scholar
• Molina , P. ; Diaz , I. ; Tfirraga , A. Synthesis of pyrrolo [2,1-c][1,4]benzo diazepines via an intramolecular aza-Wittig reaction: Synthesis of the antibiotic DC-81 . Tetrahedron 1995 , 51 , 5617 – 5630 .
   Google Scholar
• Fresneda , P. M. ; Molina , P. Application of iminophosphorane-based methodologies for the synthesis of natural products . Synlett 2004 , 1 , 1 – 17 .
   Google Scholar
• Padwa , A. ; Hornbuckle , S. F. ; Zhang , Z. ; Zhi , L. Synthesis of 1,3-diketones using α-diazo ketones and aldehydes in the presence of tin(II) chloride . J. Org. Chem. 1990 , 55 , 5299 – 5301 .
   Google Scholar
• Eguchi , S. ; Yamashita , K. ; Matsushita , Y. ; Kakehi , A. Facile synthesis of 1,4-benzodiazepin-5-one derivatives via intramolecular aza-Wittig reaction: Application to an efficient synthesis of O-benzyl DC-81 . J. Org. Chem. 1995 , 60 , 4006 – 4012 .
   Google Scholar