17.5. 4 Seven-Membered Hetarenes with Two or More Heteroatoms (Update 2013)
Book
Editors: Banert, K.; Drabowicz, J.; Oestreich, M.; Plietker, B. J.; Ramsden, C.; Schaumann, E.; Stoltz, B. M.; Weinreb, S. M.
Title: Knowledge Updates 2013/2
Print ISBN: 9783131727619; Online ISBN: 9783132401440; Book DOI: 10.1055/b-003-128236
1st edition © 2013 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G. A.; Reider, P. J.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract
This update deals with important general methods for the synthesis of diazepines, benzodiazepines, and dibenzodiazepines that have not been discussed in the earlier Science of Synthesis Section 17.5 or in Houben–Weyl, Vol. E 9d. Literature published up to 2011 is reviewed.
Key words
diazepines - benzodiazepines - dibenzodiazepines - diazepinones - ring closure - condensation reactions - copper-catalyzed cyclization - palladium-catalyzed cyclization- 1 Joseph CG, Wilson KR, Wood MS, Sorenson NB, Phan DV, Xiang Z, Witek RM, Haskell-Luevano C. J. Med. Chem. 2008; 51: 1423
- 2 Gatta E, Cupello A, Di Braccio M, Grossi G, Ferruzzi R, Roma G, Robello M. Neuroscience (Amsterdam, Neth.) 2010; 166: 917
- 9 Horváth EJ, Horváth K, Hámori T, Fekete MIK, Sólyom S, Palkovits M. Prog. Neurobiol. (Oxford, U. K.) 2000; 60: 309
- 10 Zhang N, Chen H.-M, Sood R, Kalicharran K, Fattom AI, Naso RB, Barnard DL, Sidwell RW, Hosmane RS. Bioorg. Med. Chem. Lett. 2002; 12: 3391
- 11 Zhang N, Chen H.-M, Koch V, Schmitz H, Liao C.-L, Bretner M, Bhadti VS, Fattom AI, Naso RB, Hosmane RS, Borowski P. J. Med. Chem. 2003; 46: 4149
- 12 Andronati S, Semenishyna E, Pavlovsky V, Simonov Y, Makan S, Boyko I, Burenkova N, Gdaniec M, Cardinael P, Bouillon J.-P, Mazepa A. Eur. J. Med. Chem. 2010; 45: 1346
- 13 Su J, Tang H, McKittrick BA, Burnett DA, Zhang H, Smith-Torhan A, Fawzi A, Lachowicz J. Bioorg. Med. Chem. Lett. 2006; 16: 4548
- 14 Sasikumar TK, Burnett DA, Zhang H, Smith-Torhan A, Fawzi A, Lachowicz JE. Bioorg. Med. Chem. Lett. 2006; 16: 4543
- 15 Al-Tel TH, Al-Qawasmeh RA, Schmidt MF, Al-Aboudi A, Rao SN, Sabri SS, Voelter W. J. Med. Chem. 2009; 52: 6484
- 16 Henderson EA, Alber DG, Baxter RC, Bithell SK, Budworth J, Carter MC, Chubb A, Cockerill GS, Dowdell VCL, Fraser IJ, Harris RA, Keegan SJ, Kelsey RD, Lumley JA, Stables JN, Weerasekera N, Wilson LJ, Powell KL. J. Med. Chem. 2007; 50: 1685
- 17 Kovač T, Oklobdžija M, Comisso G, Decorte E, Fajdiga T, Moimas F, Angeli C, Zonno F, Toso R, Šunjić V. J. Heterocycl. Chem. 1983; 20: 1339
- 18 Sakaki J, Kishida M, Konishi K, Gunji H, Toyao A, Matsumoto Y, Kanazawa T, Uchiyama H, Fukaya H, Mitani H, Arai Y, Kimura M. Bioorg. Med. Chem. Lett. 2007; 17: 4804
- 19 Sakaki J, Konishi K, Kishida M, Gunji H, Kanazawa T, Uchiyama H, Fukaya H, Mitani H, Kimura M. Bioorg. Med. Chem. Lett. 2007; 17: 4808
- 20 Churcher I, Ashton K, Butcher JW, Clarke EE, Harrison T, Lewis HD, Owens AP, Teall MR, Williams S, Wrigley JDJ. Bioorg. Med. Chem. Lett. 2003; 13: 179
- 21 Churcher I, Williams S, Kerrad S, Harrison T, Castro JL, Shearman MS, Lewis HD, Clarke EE, Wrigley JDJ, Beher D, Tang YS, Liu W. J. Med. Chem. 2003; 46: 2275
- 22 Akgün E, Körner M, Gao F, Harkumar KG, Waser B, Reubi JC, Portoghese PS, Miller LJ. J. Med. Chem. 2009; 52: 2138
- 23 Hasvold LA, Wang L, Przytulinska M, Xiao Z, Chen Z, Gu W.-Z, Merta PJ, Xue J, Kovar P, Zhang H, Park C, Sowin TJ, Rosenberg SH, Lin N.-H. Bioorg. Med. Chem. Lett. 2008; 18: 2311
- 24 Wang L, Sullivan GM, Hexamer LA, Hasvold LA, Thalji R, Przytulinska M, Tao Z.-F, Li G, Chen Z, Xiao Z, Gu W.-Z, Xue J, Bui M.-H, Merta P, Kovar P, Bouska JJ, Zhang H, Park C, Stewart KD, Sham HL, Sowin TJ, Rosenberg SH, Lin N.-H. J. Med. Chem. 2007; 50: 4162
- 25 Loudni L, Roche J, Potiron V, Clarhaut J, Bachmann C, Gesson J.-P, Tranoy-Opalinski I. Bioorg. Med. Chem. Lett. 2007; 17: 4819
-
26 Basolo L, Beccalli EM, Borsini E, Broggini G, Khansaa M, Rigamonti M. Eur. J. Org. Chem. 2010; 1694
- 27 Pettersson H, Bülow A, Ek F, Jensen J, Ottesen LK, Fejzic A, Ma J.-N, Del Tredici AL, Currier EA, Gardell LR, Tabatabaei A, Craig D, McFarland K, Ott TR, Piu F, Burstein ES, Olsson R. J. Med. Chem. 2009; 52: 1975
- 28 Janciene R, Stumbreviciute Z, Podeniene D, Puodziunaite BD, Black S, Husbands SM. J. Heterocycl. Chem. 2006; 43: 979
- 30 Gitto R, Orlando V, Quartarone S, De Sarro G, De Sarro A, Russo E, Ferreri G, Chimirri A. J. Med. Chem. 2003; 46: 3758
- 34 Zappalà M, Postorino G, Micale N, Caccamese S, Parrinello N, Grazioso G, Roda G, Menniti FS, De Sarro G, Grasso S. J. Med. Chem. 2006; 49: 575
- 35 Zappalà M, Pellicanò A, Micale N, Menniti FS, Ferreri G, De Sarro G, Grasso S, De Micheli C. Bioorg. Med. Chem. Lett. 2006; 16: 167
- 36 Micale N, Colleoni S, Postorino G, Pellicanò A, Zappalà M, Lazzaro J, Diana V, Cagnotto A, Mennini T, Grasso S. Bioorg. Med. Chem. 2008; 16: 2200
- 43 Chimirri A, De Sarro G, De Sarro A, Gitto R, Quartarone S, Zappalà M, Constanti A, Libri V. J. Med. Chem. 1998; 41: 3409
- 44 Elger B, Huth A, Neuhaus R, Ottow E, Schneider H, Seilheimer B, Turski L. J. Med. Chem. 2005; 48: 4618
- 45 Csuzdi E, Migléczi K, Hazai I, Berzsenyi P, Pallagi I, Horváth G, Lengyel G, Sólyom S. Bioorg. Med. Chem. Lett. 2005; 15: 4662
- 49 Magano J, Acciacca A, Akin A, Collman BM, Conway B, Waldo M, Chen MH, Mennen KE. Org. Process Res. Dev. 2009; 13: 555
- 59 Bonacorso HG, Lourega RV, Porte LMF, Deon ED, Zanatta N, Flores AFC, Martins MAP. J. Heterocycl. Chem. 2009; 46: 603
- 69 Anzini M, Braile C, Valenti S, Cappelli A, Vomero S, Marinelli L, Limongelli V, Novellino E, Betti L, Giannaccini G, Lucacchini A, Ghelardini C, Norcini M, Makovec F, Giorgi G, Fryer RI. J. Med. Chem. 2008; 51: 4730