Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylazines

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Title in English Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylazines.
Authors

ZACHOVÁ Hana MAN Stanislav NEČAS Marek POTÁČEK Milan

Year of publication 2005
Type Article in Periodical
Magazine / Source European Journal of Organic Chemistry
MU Faculty or unit

Faculty of Science

Citation
Field Organic chemistry
Keywords allenes; cycloaddition; nitrogen heterocycles; sigmatropic rearrangement; polycycles
Description A thermally initiated intramolecular criss-cross cycloaddition of 3-substituted symmetrical homoallenyl azines (5) was searched. Their cyclization led to interesting new fused heterocyclic systems consisting of four five-membered rings with two nitrogen heteroatoms (6). The preparation of azines was based on application of homoallenylaldehydes (4) in reaction with hydrazine. The homoallenylaldehydes (4) were prepared by Claisen rearrangement of new N,N-disubstituted 4-[(2-methylprop-1-en-1-yl)oxy]but-2-yn)-1-amines (3a-f) prepared by Mannich reaction from 2-methylprop-1-en-1-yl prop-2-yn-1-yl ether (2). The success in the reaction was based on improved solventless procedure of 1-chloro-2-methylpropyl prop-2-yn-1-yl ether (1) synthesis and its conversion to fully isolable 2-methylprop-1-en-1-yl prop-2-yn-1-yl ether (2) in high yield.
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