Synthetic Pathways to Pyrido[3,4-c]pyridazines and Their Polycyclic Derivatives

References (61)

1. 1 Walsh, 2015, Nature loves nitrogen heterocycles [DOI]
2. 2 Vitaku, 2014, Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals [DOI]
3. 3 Pitt, 2009, Heteroaromatic Rings of the Future [DOI]
4. 4 Wojcicka, 2018, Synthesis and Biological Activity of Pyridopyridazine Derivatives: A Mini Review [DOI]
5. 5 Thorimbert, 2019, ‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space [DOI]
6. 6 Leach, 2011, Quantitatively Interpreted Enhanced Inhibition of Cytochrome P450s by Heteroaromatic Rings Containing Nitrogen [DOI]
7. 7 Graton, 2016, Hydrogen-Bond Accepting Properties of New Heteroaromatic Ring Chemical Motifs: A Theoretical Study [DOI]
8. 8 Yamamoto, Y., and Shinkai, I. (2004). Product Class 18: Pyridopyridazines. Science of Synthesis, 16: Category 2, Hetarenes and Related Ring Systems, Thieme. [DOI]
9. 9 Ibrahim, 2015, “Pyridopyridazine”: A Versatile Nucleus in Pharmaceutical Field
10. 10 Atkinson, C.M., and Biddle, B.N. (1966). Triazaphenanthrenes. Part VI. Further observations on the Widman-Stoermer and Borsche reactions. J. Chem. Soc. C, 2053–2060. [DOI]
11. 11 Stockmann, 2011, 7-Azacinnolin-4(1H)-one preparation and NMR studies of tautomery [DOI]
12. 12 Bundy, G.L. (2002). Heterocycle Carboxamides as Antiviral Agents (WO 02/04444), World Intellectual Property Organisation.
13. 13 Kochhar, 1969, 8-chloro-4-hydroxy-3-methyl-pyrido[3,4-c]pyridazine [DOI]
14. 14 Jones, 1978, A synthesis of annulated pyridazines by cycloaddition of azodicarboxylates to vinylpyridines [DOI]
15. 15 Jones, 1979, The synthesis of annulated pyridazines by cycloaddition of azodicarboxylates to vinyl heterocycles [DOI]
16. 16 Gao, Y. (2007). Piperazinyl Oxoalkyl Tetrahydroisoquinolines and Related Analogues (WO 2007/106349), World Intellectual Property Organization.
17. 17 Zhao, L., Jin, L., and Jin, Y. (2013). 5,6,7,8-Tetrahydro-2H-Pyridineo [3,4-c] Pyridine Synthesis Method of Azine-3-Ketones (CN 102924452 A), State Intellectual Property Office of the People’s Republic of China.
18. 18 Ashton, W.T., Caldwell, C.G., Duffy, J.L., Mathvink, R.J., Wang, L., and Weber, A. (2004). 3-Amino-4-Phenylbutanoic Acid Derivatives as Dipeptidyl Peptidase Inhibitors for the Treatment or Prevention of Diabetes (WO 2004/069162), World Intellectual Property Organization.
19. 19 Wan, H., Geng, M., and Yu Cheng, C. (2016). A Class of Compounds with Kinase Inhibitory Activity, Preparation Method and Uses (201610383073.2), State Intellectual Property Office of the People’s Republic of China.
20. 20 Szabo, G., and Potor, A. (2021). Naphthyridine and Pyrido[3,4-c]pyridazine Derivatives as GABAa α5 Receptor Modulators (WO 2021/191838), World Intellectual Property Organization.
21. 21 Lange, U., Ochse, M., van der Kam, E., van Bergeijk, J., Turner, S., Oellien, F., Walleser, P., Amberg, W., Hornberger, W., and Geneste, H. (2017). Fused Heterocyclic Compounds as SlP Modulators (US 2017/0057966), United States Patent Application Publication.
22. 22 Abdelhamid, 2007, Alkylazinylcarbonitriles as building blocks in organic synthesis: Synthesis of 3-amino-7-arylhyrazonothieno-7H-[3,4-c]-pyridine-4,6-diones and pyrido-[3,4-c]-pyridazine-5-carbonitrile [DOI]
23. 23 Barsy, 2000, Studies on Polyfunctionalised Heteroaromatics: Synthesis of Several New Cinnoline and Pyrido[3,4-c]pyridazine Derivatives [DOI]
24. 24 Barsy, 2006, A Convenient and Facile Synthesis of Pyridine, Pyridazine, Pyrimido[4,5-c]pyridazine, Pyrido[3,4-c]pyridazine, 1,6-Naphthyridine and Phthalazine Derivatives
25. 25 Elnaghi, 1992, Studies on alkylheteroaromatics: A novel synthesis of pyrido[3,4-c]pyridazine derivatives
26. 26 HElnagdi, 1995, New synthetic approaches to condensed pyridazinones: Alkylpyridazinyl carbonitriles as building blocks for the synthesis of condensed pyridazinones [DOI]
27. 27 Laihia, 2004, NMR Spectroscopic and X-ray Structural Characterization of Two Diaryl Derivatives of (4-Cyano-6-methyl-3,8-dioxo-2,3,5,6,7,8-hexahydropyrido[3,4-c] Pyridazin-6-yl)hydrazono-acetic acid Ethyl Ester [DOI]
28. 28 Darwish, 2011, Enamines in Heterocyclic Synthesis: A Novel Simple and Efficient Route to Condensed Pyridazines [DOI]
29. 29 Erian, 1997, Polyfunctionally Substituted Heterocycles: Synthesis of New Polyfunctionally Substituted Phthalazines, Pyrido[3,4-c]pyridazines and Pyrazolo[3,4-c]pyridazines [DOI]
30. 30 Manhi, 1992, Studies with Polyfunctionally Substituted Heterocycles: Novel Syntheses of Pyrido[4,3-d]pyridazines and of Pyrido[3,4-d]pyridazines [DOI]
31. 31 Elghandour, 1992, Polyfunctionally Substituted Heterocycles: Synthesis of new polyfunctionally substituted phthalazines, thieno[3,4-d]pyridazines and pyrido [3,4-c]pyridazines [DOI]
32. 32 Hussein, 1995, Novel Synthesis of Pyridopyridazine, Pyrrolopyridazine and Some Pyridazine Derivatives
33. 33 Hao, X. (2021). Cinnolines as Inhibitors of HPK 1 (WO 2021/004535), World Intellectual Property Organization.
34. 34 Berger, 1982, Diels-Alder-Reaktionen mit cyclischen Iminen, 3. Mitt. Cycloaddition von Iminen an Tetrazine [DOI]
35. 35 Atkinson, C.M., and Mattocks, A.R. (1957). 733. Triazaphenanthrenes. Part II. Derivatives of 10-phenyl- 1:2:9-triazaphenanthrene. J. Chem. Soc., 3722–3726. [DOI]
36. 36 Atkinson, C.M., and Mattocks, A.R. (1962). 320. Triazaphenanthrenes. Part V. The site of quaternisation in some triazaphenanthrene methiodides. J. Chem. Soc., 1671–1678. [DOI]
37. 37 Cajipe, 1975, Reaction of aminoquinones and related vinylogous amides with nitrous acid. Synthesis and chemistry of cyclic diazo ketones [DOI]
38. 38 Proshchenkova, 2021, Synthesis of 4-Ethoxycarbonyl(cyano)-β-Carbolines via Thermolysis of 4-Aryl-3(5)-Azidopyridine Derivatives and the Study of their Optical and Hypoglycemic Properties [DOI]
39. 39 Barton, 1975, Synthesis of the monoazabiphenylenes [DOI]
40. 40 Iqbal, 2006, Photochemistry of phenazopyridine hydrochloride
41. 41 Ibrahim, 2017, Gas-phase pyrolysis of arylazonicotinates and nicotinonitriles: Routes towards new aminopyridine and pyrido[3,4-c]cinnoline derivatives [DOI]
42. 42 Jerchel, 1956, 2.3-Azadiphenylen-tetrazoliumsalze und Triazaphenanthrene [DOI]
43. 43 Ames, 1976, Cinnolines. Part XVII. Reactions of 4-chlorocinnoline-3-carbonitrile and preparation of 2,3-dihydro-3-imino-1H-pyrazolo[4,3-c]cinnolines [DOI]
44. 44 Goerlitzer, 1996, Furo-, Pyrrolo- and Pyridazino(3,4-c)quinolines
45. 45 Goerlitzer, 2002, Pyridazino[3,4-c]quinolines and Pyridazino[4,5-c]quinolines—Synthesis and Investigation of Lipoxygenase Inhibition
46. 46 Seitz, 1976, Inverse” Diels-Alder-Additionen, 4. Mitt.: π-Elektronenreiche, benzokondensierte Heteroaromaten als „inverse” Dienophile [DOI]
47. 47 Pindur, 1994, Cyclization Reactions of 2,2’-Bis-N-methylindolyl to Potential Protein Kinase C Inhibitors [DOI]
48. 48 MacBride, 1974, Synthesis of 2,7-diazabiphenylene by thermal extrusion of nitrogen from 2,7,9,10-tetra-azaphenanthrene [DOI]
49. 49 Kanoktanaporn, S., and MacBride, J.A.H. (1978). Preparation of ring-fused pyridazines by reduction of 3,3′-dinitro-4,4′-bipyridyl and 3,3′-dinitro-4,4′-biquinolyl. J. Chem. Soc. Perkin Trans. 1, 1126–1131. [DOI]
50. 50 Kanoktanaporn, 1980, Biphenylenes and Heterocyclic Analogs of Biphenylene. Part II. Preparation of f 2,7-Diazabiphenylene, its Quaternary Salts, and an Unstable Angular Dibenzo-derivative; X-ray Crystal Structure of 2-Allyl-2-azonia-7-azabiphenylene bromi
51. 51 Kaczmarek, 1987, Bipyridines. XIX. Synthesis of some novel 2,7,9,10-Tetraazaphenanthrene derivatives [DOI]
52. 52 MacBride, 1981, Synthesis of 1.6-Diazabiphenylene by Flash Vacuum Pyrolysis of 2,5,9,10-tetra-azaphenanthrene; NMR Evidence for Rehybridisation in Biphenylenes [DOI]
53. 53 Stockmann, 2008, Preparation of new pyrido[3,4-b]thienopyrroles and pyrido[4,3-e]thienopyridazines [DOI]
54. 54 Stockmann, 2008, Preparation of novel pyridine-fused tris-heterocycles; pyrido[4,3-e]pyrrolo-/pyrido[4,3-e]furano[2,3-c]pyridazines and pyrido[3,4-b]pyrrolo[3,2-d]pyrrole [DOI]
55. 55 Barawkar, D., Bende, T., Zahler, R., Bandyopadhyay, A., Sarangthem, R.S., Doshi, J., Waman, Y., Jadhav, R., and Singh, U.P. (2012). Substituted Fused Tricyclic Compounds, Compositions and Medicinal Applications Thereof (WO 2012/127506), World Intellectual Property Organization.
56. 56 Llobat, A., Escorihuela, J., Sedgwick, D.M., Rodenes, M., Román, R., Soloshonok, V.A., Han, J., Medio-Simón, M., and Fustero, S. (2020). The Ruthenium-Catalyzed Domino Cross Enyne Metathesis/Ring-Closing Metathesis in the Synthesis of Enantioenriched Nitrogen-Containing Heterocycles. Eur. J. Org. Chem., 4193–4207. [DOI]
57. 57 Elix, 1971, Preparation and X-ray structure of the 8a-azonia-3,4-diazaphenanthrene cation [DOI]
58. 58 Merz, 1970, Reaktionen des thebains mit azodicarbonsäureestern [DOI]
59. 59 Giger, 1973, Synthesis and reactions of the Diels-Alder adduct of thebaine with 4-phenyl-1,2,4-triazoline-3,5-dione [DOI]
60. 60 Marton, 1996, Reaction of morphinan-6,8-dienes with azadienophiles [DOI]
61. 61 Csutoras, 1997, Syntheses and transformations of novel nitrogen and sulfur containing morphinanedienes [DOI]

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