Abstract
In this work different strategies for synthesis of allyl hydrazine were investigated and compared in terms of selectivity, reproducibility and yield. The motivation of this study was mainly the low selectivity and reproducibility of the classical synthetic route, which utilizes allyl halide and hydrazine hydrate as parent substances. In search of more effective methods we have tested the potential of protecting group strategy by exploiting different Boc-hydrazines. We conclude that the approach overcomes the shortcomings of the classical method, as the aforementioned essential synthesis characteristics can be considerably improved. The best results were obtained by employing the route starting with tri-Boc-hydrazine.
Highlights
Like other substituted hydrazines allyl hydrazine has a number of applications in pharmacy, agricultural chemistry and organic synthesis, e.g. as a parent substance for synthesis of target compounds.[1]
In this work we compare the synthesis of allyl hydrazine via conventional method to these of protective group strategy, starting with Boc-hydrazine, 1, 2-bis-Boc-hydrazine and 1,1,2-tri-Boc-hydrazine
For the first time protecting group strategy was successfully applied for the synthesis of allyl hydrazine
Summary
Like other substituted hydrazines allyl hydrazine has a number of applications in pharmacy, agricultural chemistry and organic synthesis, e.g. as a parent substance for synthesis of target compounds.[1]. A mixture of allyl and diallyl hydrazines was formed. The mixture was separated by column chromatography, yielding 50% of 1-allyl-1, 2-bis-Boc-hydrazine. A similar approach for the synthesis of allyl hydrazine has been proposed recently.[9] The work describes the allylation of 1, 2-bis-Boc-hydrazine under phase transfer catalytic conditions (5%NaOH/toluene/TBAHS, rt, 2.5 h, 71% yield), which differ from the conditions applied in our experiment.
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