Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines

[1] Brandsma, L. (2001). Unsaturated carbanions, heterocumulenes and thiocarbonyl compounds — new routes to heterocycles. European Journal of Organic Chemistry, 2001, 4569–4581. DOI: 10.1002/1099-0690(200112)2001:24〈4569::aid-ejoc 4569〉3.0.CO;2-w. Suche in Google Scholar

[2] Brandsma, L. (2004). Synthesis of acetylenes, allenes and cumulenes: Methods and techniques. Oxford, UK: Elsevier. Suche in Google Scholar

[3] Brandsma, L., & Nedolya, N. A. (2004). Allenic compounds and isothiocyanates as key building units in the synthesis of heterocycles. Synthesis, 2004, 735–745. DOI: 10.1055/s-2004-816005. 10.1055/s-2004-816005Suche in Google Scholar

[4] Brasholz, M., Reissig, H. U., & Zimmer, R. (2009). Sugars, alkaloids, and heteroaromatics: exploring heterocyclic chemistry with alkoxyallenes. Accounts of Chemical Research, 42, 45–56. DOI: 10.1021/ar800011h. http://dx.doi.org/10.1021/ar800011h10.1021/ar800011hSuche in Google Scholar

[5] Bruker AXS (1997). SHELXTL, Version 5.10. An integrated system for solving and refining crystal structures from diffraction data. Madison, WI, USA: Bruker AXS. Suche in Google Scholar

[6] Galeta, J., Man, S., & Potáček, M. (2009). Non-symmetrical allenyl azines and their transformations leading to new heterocyclic skeletons. ARKIVOC, 2009, 6, 245–259. 10.3998/ark.5550190.0010.625Suche in Google Scholar

[7] Galeta, J., Man, S., Bouillon, J. P., & Potáček, M. (2011). Unexpected heterocyclic products from cycloaddition reactions of nonsymmetrical allenyl aldoketazines with substituted alkynes. European Journal of Organic Chemistry, 2011, 392–398. DOI: 10.1002/ejoc.201001044. 10.1002/ejoc.201001044Suche in Google Scholar

[8] Galeta, J., & Potáček, M. (2012). Substituted diazatetracyclo [4.4.0.13,10.15,8]dodecanes as stable caged proton sponges. The Journal of Organic Chemistry, 77, 1010–1017. DOI: 10.1021/jo202235f. http://dx.doi.org/10.1021/jo202235f10.1021/jo202235fSuche in Google Scholar

[9] Galeta, J., Man, S., & Potáček, M. (2013). Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones. Chemical Papers, 67, 29–39. DOI: 10.2478/s11696-012-0215-6. 10.2478/s11696-012-0215-6Suche in Google Scholar

[10] Koziara, A., Turski, K., & Zwierzak, A. (1986). A general synthesis of unsymmetrical azines via N-(diethoxyphosphinyl)-hydrazones. Synthesis, 1986, 298–301. DOI: 10.1055/s-1986-31589. 10.1055/s-1986-31589Suche in Google Scholar

[11] Krause, N., & Hashmi, A. S. K. (2004). Modern allene chemistry. Weinheim, Germany: Wiley-VCH. http://dx.doi.org/10.1002/978352761957310.1002/9783527619573Suche in Google Scholar

[12] Man, S., Kulhánek, P., Potáček, M., & Nečas, M. (2002). New fused heterocycles by combined intra-intermolecular crisscross cycloaddition of nonsymmetrical azines. Tetrahedron Letters, 43, 6431–6433. DOI: 10.1016/s0040-4039(02)01378-3. http://dx.doi.org/10.1016/S0040-4039(02)01378-310.1016/S0040-4039(02)01378-3Suche in Google Scholar

[13] Man, S., Bouillon, J. P., Nečas, M., & Potáček, M. (2004). Combined intra-intermolecular criss-cross cycloaddition of a new fluorinated unsymmetrical allenylazine with alkynes. Tetrahedron Letters, 45, 9419–9421. DOI: 10.1016/j.tetlet.2004.10.107. http://dx.doi.org/10.1016/j.tetlet.2004.10.10710.1016/j.tetlet.2004.10.107Suche in Google Scholar

[14] Man, S., Nečas, M., Bouillon, J. P., Baillia, H., Harakat, D., & Potáček, M. (2005). New intra-intermolecular criss-cross cycloaddition of unsymmetrical allenylazines with alkynes lead ing to three fused five-membered heterocycles. Tetrahedron, 61, 2387–2393. DOI: 10.1016/j.tet.2005.01.020. http://dx.doi.org/10.1016/j.tet.2005.01.02010.1016/j.tet.2005.01.020Suche in Google Scholar

[15] Schweizer, E. E., & Lee, K. J. (1984). Reactions of azines. 8. Synthesis and thermal rearrangement of 1-oxo-3,4-diaza-2,4,6-heptatrienes and 1-oxo-3,4-diaza-2,4,6,7-octatetraenes (allenyl azines). The Journal of Organic Chemistry, 49, 1959–1964. DOI: 10.1021/jo00185a025. http://dx.doi.org/10.1021/jo00185a02510.1021/jo00185a025Suche in Google Scholar

[16] Schweizer, E. E., Hayes, J. E., Hirwe, S. N., & Rheingold, A. L. (1987). Reactions of azines. 9. Preparation of 4,5-dihydropyrazolo[1,5-a]pyridines, 6,7-dihydropyrazolo[1,5-a]pyridines, and pyrazolo[1,5-a]pyridines. The Journal of Organic Chemistry, 52, 1319–1324. DOI: 10.1021/jo00383a028. http://dx.doi.org/10.1021/jo00383a02810.1021/jo00383a028Suche in Google Scholar

[17] Zachová, H., Man, S., Nečas, M., & Potáček, M. (2005). Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylaldazines. European Journal of Organic Chemistry, 2005, 2548–2557. DOI: 10.1002/ejoc.200400814. 10.1002/ejoc.200400814Suche in Google Scholar

[18] Zachová, H., Marek, R., Man, S., Taraba, J., & Potáček, M. (2006). A new rearrangement of fused tetracyclic heterocycles in an acidic medium in the presence of NaBH3CN. Tetrahedron Letters, 47, 8157–8159. DOI: 10.1016/j.tetlet.2006.09.030. http://dx.doi.org/10.1016/j.tetlet.2006.09.03010.1016/j.tetlet.2006.09.030Suche in Google Scholar

[19] Zachová, H., Man, S., Taraba, J., & Potáček, M. (2009). Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of ‘proton sponge’. Tetrahedron, 65, 792–797. DOI: 10.1016/j.tet.2008.11.057. http://dx.doi.org/10.1016/j.tet.2008.11.05710.1016/j.tet.2008.11.057Suche in Google Scholar

[20] Zimmer, R. (1993). Alkoxyallenes — building blocks in organic synthesis. Synthesis, 1993, 165–178. DOI: 10.1055/s-1993-25823. 10.1055/s-1993-25823Suche in Google Scholar

[21] Zwierzak, A., & Sulewska, A. (1976). Solid-liquid phasetransfer-catalysed phosphorylation of hydrazine. Preparation of dialkyl phosphorohydrazidates and N,N′-bis[dialkoxyphosphoryl] hydrazines. Synthesis, 1976, 835–837. DOI: 10.1055/s-1976-25385. 10.1055/s-1976-25385Suche in Google Scholar