Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines

This paper deals with the preparation of a variously substituted non-symmetrical azine set. The starting molecule for their preparation was a protected hydrazone. The protection was performed applying Zwierzak’s method. This procedure is based on the transfer of hydrazine to diethylhydrazidophosphate, which reacts with aldehydes to produce protected hydrazones. In the second step of the procedure, under the action of sodium hydride, the addition of another aldehyde affords non-symmetrical azines in the reaction with the protected hydrazine. The procedure was shown to be a useful and effective method. In this, the second part of our study, we present results devoted to the preparation and full identification of non-symmetrical azines.

[1]  H. Reissig,et al.  Alkoxyallenes as building blocks for organic synthesis. , 2014, Chemical Society reviews.

[2]  J. Galeta,et al.  Substituted diazatetracyclo[4.4.0.1(3,10).1(5,8)]dodecanes as stable caged proton sponges. , 2012, The Journal of organic chemistry.

[3]  J. Galeta,et al.  Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones , 2012, Chemical Papers.

[4]  J. Galeta,et al.  Unexpected Heterocyclic Products from Cycloaddition Reactions of Nonsymmetrical Allenyl Aldoketazines with Substituted Alkynes , 2011 .

[5]  H. Reissig,et al.  Sugars, Alkaloids, and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes , 2009 .

[6]  J. Galeta,et al.  Non-symmetrical allenyl azines and their transformations leading to new heterocyclic skeletons , 2009 .

[7]  M. Potáček,et al.  Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of ‘proton sponge’ , 2009 .

[8]  R. Marek,et al.  A new rearrangement of fused tetracyclic heterocycles in an acidic medium in the presence of NaBH3CN , 2006 .

[9]  M. Potáček,et al.  Fused Tetracyclic Heterocycles by Thermally Initiated Intramolecular Criss-Cross Cycloaddition of 3-Substituted Homoallenylaldazines , 2005 .

[10]  M. Potáček,et al.  New intra–intermolecular criss-cross cycloaddition of unsymmetrical allenylazines with alkynes leading to three fused five-membered heterocycles , 2005 .

[11]  M. Potáček,et al.  Combined intra-intermolecular criss-cross cycloaddition of a new fluorinated unsymmetrical allenylazine with alkynes , 2004 .

[12]  A. Hashmi,et al.  Modern Allene Chemistry , 2004 .

[13]  N. Nedolya,et al.  Allenic Compounds and Isothiocyanates as Key Building Units in the Synthesis of Heterocycles , 2004 .

[14]  L. Brandsma.  Synthesis of acetylenes, allenes and cumulenes : methods and techniques , 2004 .

[15]  A. Zwierzak,et al.  Solid-Liquid Phase-Transfer-Catalysed Phosphorylation of Hydrazine. Preparation of Dialkyl Phosphorohydrazidates and N,N′-Bis[dialkoxyphosphoryl]hydrazines , 2002 .

[16]  P. Kulhánek,et al.  New fused heterocycles by combined intra-intermolecular criss-cross cycloaddition of nonsymmetrical azines ☆ , 2002 .

[17]  L. Brandsma.  Unsaturated Carbanions, Heterocumulenes and Thiocarbonyl Compounds − New Routes to Heterocycles , 2001 .

[18]  J. E. Hayes,et al.  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 , 1987 .

[19]  A. Koziara,et al.  A General Synthesis of Unsymmetrical Azines via N-(Diethoxyphosphinyl)-hydrazones , 1986 .

[20]  E. Schweizer,et al.  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) , 1984 .

[21]  J. Hartwell,et al.  DIRECT RING CLOSURE THROUGH THE NITRO GROUP. ISOMER FORMATION IN THE SYNTHESIS OF UNSYMMETRICAL PHENAZINES, AND SOME GENERAL OBSERVATIONS ON THE PHENAZINE SYNTHESES , 1951 .