Heterocyclic Synthesis Using Nitrilimines: Part 7. Synthesis of Some New Substituted 1,2,4,8-TETRAAZASPIRO[4.5]DEC-2-ENES

Abstract

A series of new l, 2,4,8-tetrazaspiro[4.5]dec-2-enes 4a-r were synthesized from the reaction of corresponding hydrazonoyl halides i with substituted heterocyclic oximes 3. The structures of the synthesized compounds were confirmed by their elemental analysis and spectral data.

Synthesis of Nitrogen-Containing Dispiroheterocycles (Iii) Using Nitrilimines

“…the e-5 and C-8 signals (spiro carbons) were found at about 97-89 ppm. This is similar to reported values for spiro carbons flanked by two nitrogen atoms in fivemembered heterocycles [4][5][6], which provides strong evidence in support of the structures Va-j rather than the six-membered structure IVa-j, which is expected to have a C-6 and C-9 signal at about 70 ppm [2], The signal at about 14 7 ppm was attributed to the e=N of the triazole ring. This assignment is in good agreement with literature data for azomethine carbons.…”

“…As part of our continuing interest in the construction of spiroheterocyclic systems by means of the nitrilimine 1,3-dipolar cycloaddition methodology [3][4][5][6], we reported here the reaction of Csubstituted-N-arylnitriliinines II with l,4-cyclohexar1edione benzoylhydrazone III in an attempt to synthesize the hitherto unknown hexaazadispiroheterocyclic compounds Va-j with the aim of investigating their biological activities.…”

Synthesis of nitrogen-containing dispiroheterocycles (1) using nitrilimines

“…Examples of these modes of reactions were recently reviewed by Ferwanah et al 13 for the reactions of hydrazones and oximes with nitrilimines and nitrile oxides. The synthesis of different spiroheterocycles I-III was recently reported using nitrilimines and cycloalkanone hydrazones or oximes [14][15][16][17] ( Figure 1). As part of our program aimed at developing new biologically active compounds, we report here the synthesis of the hitherto unknown dispiroheterocyclic compounds 4a-k from the reaction between different nitrilimines 2 and 1,4-cyclohexanedione methyl hydrazone 3.…”