tailieunhanh - Synthesis of several aromatic aldazines

Ten aromatic aldazines: 4-nitrobenzal-, 3-nitrobenzal-, 2-nitrobenzal-, 4-dimethylaminobenzal-, 4-methoxybenzal-, 3-methoxybenzal-, 4-fluorobenzal-, 4-chlorobenzal-, 4-bromobenzaldazine and 7-carboxymethoxy-6-hydroxy-3-sulfoquinolin-5-carbaldazine, were synthesized by condensing two equivalents of an appropriate aldehyde with one equivalent of hydrazine hydrate. The structure of the received aldazines was determined by IR, 1H-NMR and ESI MS spectra. | JOURNAL OF SCIENCE OF HNUE Chemical and Biological Sci. 2012 Vol. 57 No. 8 pp. 16-21 This paper is available online at http SYNTHESIS OF SEVERAL AROMATIC ALDAZINES Le Van Co1 Nguyen Dang Dat2 and Nguyen Huu Dinh2 1 Faculty of Chemistry Tay Nguyen University 2 Faculty of Chemistry Hanoi National University of Education Abstract. Ten aromatic aldazines 4-nitrobenzal- 3-nitrobenzal- 2-nitrobenzal- 4-dimethylaminobenzal- 4-methoxybenzal- 3-methoxybenzal- 4-fluorobenzal- 4-chlorobenzal- 4-bromobenzaldazine and 7-carboxymethoxy-6-hydroxy-3-sulfoquinolin-5-carbaldazine were synthesized by condensing two equivalents of an appropriate aldehyde with one equivalent of hydrazine hydrate. The structure of the received aldazines was determined by IR 1 H-NMR and ESI MS spectra. Keywords Aldazines synthesis IR 1 H-NMR and ESI MS spectra. 1. Introduction Aldazines are functional organic compounds which are formed by a condensation reaction of two equivalents of an aldehyde with one equivalent of hydrazine 1 . Aldazines have been used for preparation of hydrazones 2 3 and diazo compounds 4 5 . They have been also used as sources for hydrazine produced in situ for example in the production of herbicide precursor 1 2 4-triazole 6 . Symmetrical and unsymmetrical aldazines are efficiently converted to 2 5-disubstituted-1 3 4-oxadiazoles by oxidation with bis trifluoroacetoxy iodobenzene BTI 7 Received July 17 2012. Accepted September 24 2012. Chemistry Subject Classification 10401. Contact Nguyen Huu Dinh e-mail address nguyenhuusp@ 16 Synthesis of several aromatic aldazines Aldazines readily participate in some pericyclic reaction variants 8 and react with isocyanate in a double 3 2 cycloaddition involving both C N bonds to form triazolotriazoles 8 In view of the above mentioned findings herein we report the synthesis of some substituted benzaldazines and polysubstituted quinoline-5-carbaldazine as precursors to the triazolotriazoles. 2. Content . .