Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 2
382
Views
19
CrossRef citations to date
0
Altmetric
SYNTHETIC COMMUNICATIONS REVIEWS

Developments in 1,2,5-triazepine chemistry: Reactions and synthetic applications

, &
Pages 93-117 | Received 08 Oct 2015, Published online: 31 Dec 2015

References

  • (a) Archer, G. A.; Sternbach, L. H. Chemistry of benzodiazepines. Chem. Rev. 1968, 68, 747–784; (b) Sternbach, L. H. The benzodiazepine story. Prog. Drug Res. 1978, 22, 229–266.
  • Deam, M. L. A simple synthesis of a 1H-1,2,4-triazepine. Synthesis 1981, 322–323.
  • Reddy, G. S.; Kumar, P. A.; Anand, R. V.; Mukkanti, K.; Reddy, P. P. An expedient entry to fused [1,2,5]-triazepine derivatives: Extension to fused [1,2,5]-oxadiazine derivatives, a new class of seven-membered heterocycles. Synlett 2009, 9, 1463–1465.
  • Demydchuk, B. A.; Brovarets, V. S.; Chernega, A. N.; Rusanov, E. B.; Drach, B. S. Regioselective annulation of seven-, eight-, and nine-membered azaheterocycles to benzimidazole starting from chlorosubstituted 2-aza-1,3-dienes. Synthesis 2006, 14, 2323–2326.
  • Sternbach, L. H. The benzodiazepine story. J. Med. Chem. 1979, 22, 1–7.
  • Williams, M. Anxioselective anxiolytics. J. Med. Chem. 1983, 26, 619–628.
  • Snieckus, V.; Streith, J. 1,2-Diazepines: A new vista in heterocyclic chemistry. Acc. Chem. Res. 1981, 14, 348–355.
  • Itto, M. Y. A.; Hasnaoui, A.; Riahi, A.; Lavergne, J.-P. Regioselective synthesis of new biheterocyclic triazepines. Tetrahedron Lett. 1997, 38(12), 2087–2090.
  • Quan, H.-J.; Koyanagi, J.; Hagiwara, K.; Cui, X.-R.; Isshiki, Y.; Kondo, S.; Komada, F.; Saito, S. Reactions of 26-iodopseudodiosgenin and 26-iodopseudodiosgenone with various nucleophiles and pharmacological activities of the products. Chem. Pharm. Bull. 2006, 54(1), 72–79.
  • Costa, B.; Salvetti, A.; Rossi, L.; Spinetti, F.; Lena, A.; Chelli, B.; Rechichi, M.; Da Pozzo, E.; Gremigni, V.; Martini, C. Peripheral benzodiazepine receptor: Characterization in human T-lymphoma jurkat cells. Mol. Pharmacol. 2006, 69, 37–44.
  • Bolli, M. H.; Marfurt, J.; Grisostomi, C.; Boss, C.; Binkert, C.; Hess, P.; Treiber, A.; Thorin, E.; Morrison, K.; Buchmann, S.; Bur, D.; Ramuz, H.; Clozel, M.; Fischli, W.; Weller, T. Novel benzo[1,4]diazepin-2-one derivatives as endothelin receptor antagonists. J. Med. Chem. 2004, 47, 2776–2795.
  • Torres, S. R. R.; Nardi, G. M.; Ferrara, P.; Ribeiro-do-Valle, R. M.; Farges, R. C. Potential role of peripheral benzodiazepine receptors in inflammatory responses. Eur. J. Pharmacol. 1999, 385, R1–R2.
  • 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.
  • Keating, T. A.; Armstrong, R. W. A remarkable two-step synthesis of diverse 1,4-benzodiazepine-2,5-diones using the Ugi four-component condensation. J. Org. Chem. 1996, 61, 8935–8939.
  • Webb, R. R.; Barker, P. R.; Baier, M.; Reynolds, M. E.; Robarge, K. D.; Blackburn, B. K.; Tichler, M. H.; Weese, K. J. Mono-N-alkylation of anthranilamides via quinazolinones: An efficient synthesis of G5598, a benzodiazepine dione gpIIbIIIa antagonist. Tetrahedron Lett. 1994, 35, 2113–2116.
  • (a) Richter, P. H.; Scheefeldt, U. Synthesis and biological activity of 5-phenyl-1,3,4-benzotriazepines, 25: Synthesis of (1,2,4)triazolo(4,3-a)(1,3,4)benzotriazepines and related tricyclics. Pharmazie 1991, 46, 701–705; (b) McDonald, I. M.; Austin, C.; Buck, I. M.; Dunstone, D. J.; Griffin, E.; Harper, E. A.; Hull, R. A.; Kalindjian, S. B.; Linney, I. D.; Low, C. M.; Pether, M. J.; Spencer, J.; Wright, P. T.; Adatia, T.; Bashall, A. Novel, achiral 1,3,4-benzotriazepine analogues of 1,4-benzodiazepine-based CCK2 antagonists that display high selectivity over CCK1 receptors. J. Med. Chem. 2006, 49, 2253–2261.
  • Fernandez, P.; Guillen, M. I.; Ubeda, A.; Lopez-Cremades, P.; Aller, E.; Lorenzo, A.; Molina, P.; Alcaraz, M. J. A novel indazolo-triazolo-benzotriazepine exerts anti-inflammatory effects by inhibition of cyclooxygenase-2 activity and nitric oxide synthase-2 expression. Naunyn-Schmiedeberg’s Arch. Pharmacol. 2003, 368, 26–32.
  • Ibrahim, S. M.; Baraka, M. M.; El-Sabbagh, O. I.; Kothayer, H. Synthesis of new benzotriazepin-5(2H)-one derivatives of expected antipsychotic activity. Med. Chem. Res. 2013, 22, 1488–1496.
  • McDonald, I. M.; Austin, C.; Buck, I. M.; Dunstone, D. J.; Gaffen, J.; Griffin, E.; Harper, E. A.; Hull, R. A. D.; Kalindjian, S. B.; Linney, I. D.; Low, C. M. R.; Patel, D.; Pether, M. J.; Raynor, M.; Roberts, S. P.; Shaxted, M. E.; Spencer, J.; Steel, K. I. M.; Sykes, D. A.; Wright, P. T.; Xun, W. Discovery and characterization of novel, potent, non-peptide parathyroid hormone-1 receptor antagonists. J. Med. Chem. 2007, 50, 4789–4792.
  • (a) Spencer, J.; Gaffen, J.; Griffin, E.; Harper, E. A.; Linney, I. D.; McDonald, I. M.; Roberts, S. P.; Shaxted, M. E.; Adatia, T.; Bashall, A. Achiral, selective CCK2 receptor antagonists based on a 1,3,5-benzotriazepine-2,4-dione template. Bioorg. Med. Chem. 2008, 16, 2974–2983; (b) Kaur, K.; Talele, T. T. 2D QSAR studies of 1,3,4-benzotriazepine derivatives as CCK2 receptor antagonists. J. Mol. Graphics Modell. 2008, 27, 409–420.
  • Groszkowski, W. Pyridazino[1,2-a]1,2,5-triazepines. Polish J. Pharm. Pharm. 1978, 30(5), 713–715.
  • Birkett, P. R.; Chapleo, C. B.; Mackenzie, G. Synthesis of novel imidazotriazepines and their conversion to 9-(2-ethylaminoethyl)adenine and 9-(2-ethylaminoethyl)hypoxanthine. Synthesis 1991, 10, 822–824.
  • Raboisson, P.; Norberg, B.; Casimir, J. R.; Bourguignon, J.-J. Microwave-promoted synthesis of 4,7-dihydro-1H-imidazo[4,5-e]-1,2,4-triazepin-8-ones as ring-expanded hypoxanthine analogues. Synlett 2002, 519–521.
  • Szadowska, A.; Mazur, M.; Kaminska, A.; Kusowska, J.; Winer, A. Effect of new pyrazolo[1,2-a]-1,2,5-triazepine derivatives on the central nervous system. Acta Poloniae Pharm. 1982, 39(5–6), 463–467.
  • Lenman, M. M.; Ingham, S. L.; Gani, D. Synthesis and structure of cis-peptidyl prolinamide mimetics based upon 1,2,5-triazepine-3,6-diones. Chem. Commun. 1996, (1), 85–87.
  • Lenman, M. M.; Lewis, A.; Gani, D. Synthesis of fused 1,2,5-triazepine-1,5-diones and some N2- and N3-substituted derivatives: Potential conformational mimetics for cis-peptidyl prolinamides. J. Chem. Soc., Perkin Trans. 1 1997, 16, 2297–2311.
  • Sui, Z.; Walsh, S. P. Triazepine derivatives as neurotrophic agents. US Patent 6821993B1, 2004.
  • Fischer, R.; Künzle, F. M.; Schmuz, J. US Patent 4,450,108, 1984.
  • Effland, R. C.; Davis, L.; Kapples, K. J.; Olsen, G. E. Synthesis of novel pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepines: A novel heterocyclic ring system. J. Heterocycl. Chem. 1990, 27, 1015–1019.
  • (a) Effland, R. C.; Klein, J. T.; Hamer, R. R. L. Canadian Patent CA 1262904 A2 19891114, 1989; (b) Effland, R. C.; Klein, J. T.; Hamer, R. R. L.; Lake, B. US Patent 4517195, 1985.
  • (a) Sharp, J. T. Comperhensive Heterocyclic Chemistry, vol. 7; A. R. Katritzky and C. W. Rees (Eds.) Pergamon Press, Oxford, 1984; p. 608; (b( Elattar, K. M.; Abozeid, M. A.; Mousa, I. A.; El-Mekabaty, A. Advances in 1,2,4-triazepines chemistry. RSC Advances. ID: RA-REV-10-2015-021108, Accepted.
  • Lena, G. Synthetic methods for the preparation of triazepandiones and review of their applications. Curr. Org. Chem. 2008, 12(10), 813–835.
  • Peet, N. P. The Chemistry of Heterocyclic Compounds, vol. 43(2) A. Rosowsky (Ed.); John Wiley & Sons, New York, 1984; p. 719.
  • (a) Anderson, D. J.; Hassner, A. Cycloaddition of 1-azirines to 1,2,4,5-tetrazines: Synthesis and rearrangement of 1,2,4-triazepines. J. Chem. Soc., Chem. Commun. 1974, 45b–46; (b) Johnson, G. C.; Levin, R. H. Triazacycloheptatrienes: The cycloaddition of azirines to dicarbomethoxy-s-tetrazine. Tetrahedron Lett. 1974, 15(26), 2303–2306;; (c) Nair, V. Thermally induced skeletal rearrangement in a triazepine. J. Heterocycl. Chem. 1975, 12, 183–184; (d) Takahashi, M.; Suzuki, N.; Igari, Y. The reaction of 1,2,4,5-tetrazines with 2-phenyl-1-azirine: The synthesis of 2H-1,2,4-triazepine derivatives. Bull. Chem. Soc. Jpn. 1975, 48, 2605–2606.
  • Saito, I.; Yazaki, A.; Matsuura, T. 1,2,4-Triazepines from the photochemical walk rearrangement of 3,4,7-triaza-2,4-norcaradienes. Tetrahedron Lett. 1976, 17, 2459–2462.
  • Seebacher, W.; Michl, G.; Weis, R. Synthesis of new triazepinethiones. Tetrahedron Lett. 2002, 43(42), 7481–7483.
  • Rezessy, B.; Zubovics, Z.; Kovacs, J.; Toth, G. Synthesis and structure elucidation of new thiazolotriazepines. Tetrahedron 1999, 55(18), 5909–5922.
  • Adamo, M. F. A.; Baldwin, J. E.; Adlington, R. M. Application of bis-acetylenic ketones in synthesis: One-pot preparation of the 1,2,4-triazepine and oxatriazaindenone cores. J. Org. Chem. 2005, 70(8), 3307–3308; and references cited therein.
  • Saveleva, E. A.; Rozin, Y. A.; Kodess, M. I.; Van Meervelt, L.; Dehaen, W.; Morzherina, Y. Y.; Bakulev, V. A. Synthesis of mesoionic[1,2,3] triazolo[5,1-d][1,2,5]triazepines. Tetrahedron 2004, 60, 5367–5372.
  • Zaleska, B.; Trzewik, B.; Grochowski, J.; Serda, P. A novel route to 1,2,3-thiadiazole, 1,3,4-thiadiazine, and 1,2, 5-triazepine derivatives. Synthesis 2003, (16), 2559–2563.
  • Katritzky, A. R.; Fan, W.-Q.; Greenhill, J. V. 4-(Benzotriazol-1-yl)-6H-benzo[c]tetrazolo[1,5-e][1,2,5]triazepine, a new heterocyclic ring system formed by a novel benzotriazole ring opening. J. Org. Chem. 1991, 56(3), 1299–1301.
  • Bouteau, B.; Imbs, J.-L.; Lancelot, J.-C.; Barthelmebs, M.; Robba, M. Synthesis and salidiuretic activity of 2,3-dihydro-8-(1-pyrrolyl)-1,2,4-triazolo[4,3-a]pyridines and 5,6-dihydro-4H-pyrido[2,3-c]pyrrolo[1,2-e]-1,2,5-triazepines. Chem. Pharm. Bull. 1991, 39(1), 81–85.
  • Kirchner, E.; Bretschneider, H. Über die Darstellung von 11-[3-Dimethylamino-propyl]-2,3,4-trimethoxy-11H-dibenz[c,f][1,2,5]triazepin. Monatsh. Chem. 1971, 102, 162–167.
  • Gnichtel, H.; Salem, W. I. The synthesis of 4H-1,2,5-triazepine derivatives from syn-α-amino hyrazones. Liebigs Ann. Chem. 1982, 4, 729–733.
  • Kamata, K.; Tsuge, O. Novel ring contraction of 4,6-dihydro-3,7-diphenyl-5-(p-tosyl)-1,2,5-trazepine via a chlorination. Heterocycles 1985, 23(7), 1674–1680.
  • (a) Tsuge, O.; Kamata, K. Studies of medium-membered heterocyclic compounds, II: Reaction of 5-benzyl-4,6-dihydro-3,7-diaryl-1,2,5-triazepines with halogenation reagents. Heterocycles 1975, 3(7), 547–552; (b) Tsuchiya, T.; Kurita, J.; Takayama, K. Studies on diazepines, XIII: Photochemical behavior of pyrazine, pyrimidine, and pyridazine N-imides. Chem. Pharm. Bull. 1980, 28, 2676–2681.
  • Mukai, T.; Kumagai, T.; Yamashita, Y. Cyclization and cycloaddition reactions of heteroepins, conjugated seven-membered heterocyclic compounds. Heterocycles 1981, 15(2), 1569–1617.
  • Sawanishi, H.; Saito, S.; Tsuchiya, T. Synthesis of fully unsaturated monocyclic 1,2,5-triazepines from 4-azidopyridazines. Chem. Pharm. Bull. 1988, 36(10), 4240–4243.
  • Sawanishi, H.; Saito, S.; Tsuchiya, T. Studies on seven-membered heterocycles, XXXIII: Synthesis of fully unsaturated 1,2,5-triazepines by photochemical ring expansion of 4-azidopyridazines. Chem. Pharm. Bull. 1990, 38(11), 2992–2996.
  • Viret, J.; Gabard J.; Collet, A. Practical synthesis of optically active α-hydrazino acids from α-amino acids. Tetrahedron 1987, 43, 891–894.
  • Neogi, S.; Roy, A.; Naskar, D. One-pot synthesis of new fused 4,5-bridged l,2,5-triazepine-3,6-diones, l,2,5-triazepine-3,7-diones heterocycles by Petasis reaction. J. Comb. Chem. 2010, 12, 75–83.
  • Menges, N.; Sari, O.; Abdullayev, Y.; Erdem, S. S.; Balci, M. Design and synthesis of pyrrolotriazepine derivatives: An experimental and computational study. J. Org. Chem. 2013, 78(11), 5184–5195.
  • Smejkal, T.; Muehlebach, M.; Jantsdhy, J. N-Oxy pyrazolo-triazepine-dione derivatives. WO Patent 2012/175666 A1, 2012.
  • El-Saghier, A. M. M.; Maihub, A. A.; Al-Shirayda, H. A. A novel synthesis of imidazo [2,1-d] [1,2,4] triazine and imidazo [2,1-d] [1,2,5] triazepine derivatives via ketene-N,N-acetal. Synth. Commun. 1997, 27(14), 2433–2444.
  • Savelli, F.; Boido, A.; Ciarallo, G. Synthesis of pyrido[3,2-e]pyrrolo[2,1-c][1,2,4]triazines from pyrido[3,2-e][1,2,4]triazine derivatives. J. Heterocycl. Chem. 1999, 36(4), 857–862.
  • Yavari, I.; Khalili, G.; Sadeghizadeh, F. A synthesis of highly functionalized pyrido[2,1-d][1,2,5]triazepines. Synlett 2012, 23(4), 557–558.
  • Szadowska, A.; Mazur, M.; Dzialek, S.; Kielek, M. B.; Kaminska, A. Preliminary studies on the central effects of new derivatives of pyridazino[1,2-a]-1,2,5-triazepine. Acta Poloniae Pharm. 1979, 36(4), 497–502.
  • Kibal’nyi, A. V.; Nikolyukin, Y. A.; Dulenko, V. I. Synthesis and some reactions of indolo[2,1-c]-1,4-oxazinium perchlorates. Chem. Heterocycl. Comp. 1994, 30(8), 895–900; Khim. Geterotsiklicheskikh Soedin. 1993, 8, 1041–1047.
  • Lancelot, J.-C.; Robba, M. Synthese de 6H- et de 4H-pyrido[2,3-c]pyrrolo[1,2-e]triazepines-1,2,5. Chem. Pharm. Bull. 1988, 36(7), 2381–2385.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.