Synthesis of Azinylvinylpyridazines: A General Note on the Isomerization of Hetaryldienamines
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (13) , 4423-4426
- https://doi.org/10.1021/jo960269u
Abstract
Azinyldienamines underwent Diels Alder reaction of inverse electron demand with 1,2,4,5-tetrazine diester to give azinylvinylpyridazines. Comparison of the products obtained from mono-, di-, and triazinyldienamines revealed that, in some cases, isomerization of the olefinic side chain occurred which can be rationalized by the tautomeric conditions of the intermediates bearing these azine moieties. These experimental findings supported also by semiempirical calculations suggest the importance of the influence of the hetaryl group in such isomerizations.Keywords
This publication has 14 references indexed in Scilit:
- Expected Selectivity and Unexpected Isomerization in the Inverse Diels-Alder Reaction of Azolyl DienesThe Journal of Organic Chemistry, 1995
- Synthesis, alkylation and ring opening of two differently fused pyridoquinazolonesJournal of Heterocyclic Chemistry, 1990
- 2‐Methylpyridinium salts as 1,4‐dinucleophiles. IV. Westphal condensation with 2‐alkyl‐1‐aminoazinium substratesJournal of Heterocyclic Chemistry, 1990
- Optimization of parameters for semiempirical methods I. MethodJournal of Computational Chemistry, 1989
- 2‐Methylpyridinium salts as 1,4‐dinucleophiles. Quinolizinium salts from the westphal condensationJournal of Heterocyclic Chemistry, 1985
- Reactions of halogenoquinolizinium bromides with aniline, isopropylamine and liquid ammoniaJournal of Heterocyclic Chemistry, 1983
- Reactions of halogenoquinolizinium bromides with diethylamineJournal of Heterocyclic Chemistry, 1982
- Ring openings of 3-aryltetrazolopyridinium salts with nucleophiles: synthesis of 1-(2-arl-5-tetrazolyl)-butadienes, diene ethers and dienaminesTetrahedron Letters, 1973
- Eine neue Ringöffnung an Chinoliziniumsalzen und deren FolgereaktionenEuropean Journal of Organic Chemistry, 1971
- Eine neue Synthese des Chinolizin-Ringsystems. DehydrochinoliziniumsalzeArchiv der Pharmazie, 1961