Heterocyclic synthesis using Nitrile imines. 4. synthesis of 3-substituted 1-aryl-1,2,4-triazaspiroalk-2-enes

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

“…The signal at 85-90 ppm was attributed to the C-5 (spiro carbon) of the triazole ring is of special significance. This assignment is in good agreement with literature data for spiro carbons (4,(7)(8)(9)(10). The signal at about 147 ppm was attributed to the C-3 carbon of the triazoles, and this is similar to reported values of azomethine carbons of five-membered heterocycles (7)(8)(9)(10).…”

Synthesis of nitrogen-containing dispiroheterocycles using nitrilimines (II)

“…The 13 C-NMR spectra showed all the signals expected for the proposed structures and, in particular, the C5 and C8 signals (spiro carbons) were found at about 95-85 ppm. This is similar to reported values for spiro carbons flanked by two nitrogen atoms in five-membered heterocycles, [3][4][5] which provides strong evidence in support of the structures 5a-j. The signal at about 148 ppm was attributed to the C=N of the triazole ring.…”

“…General procedure for the reaction of nitrilimines 2 with 1,4-cyclohexanedione dioxime (3) Triethylamine (0.05 mol, 7 mL) in tetrahydrofuran (10 mL) was added dropwise to stirred mixture of oxime 3 (0.025 mol) and the appropriate hydrazonoyl halides 1a-j (0.05 mol) in tetrahydrofuran (70 mL) at -5-0 °C. The reaction temperature was allowed to rise slowly to room temperature and stirring was continued over night.…”

“…1 As part of our continuing interest in the construction of spiroheterocyclic systems by means of the nitrilimine 1,3-dipolar cycloaddition methodology, 2-5 the reaction of C-substituted-N--arylnitrilimines (2) with 1,4-cyclohexanedione dioxime (3) in an attempt to synthesize the hitherto unknown hexaazadispiroheterocyclic compounds 5a-j is reported herein, with the aim of investigating their biological activities. RESULTS …”

Synthesis of Spiro‐Heterocycles with the Thiazolidinone Moiety from Nitrilimines

“…Their 13 C NMR spectra showed all the signals of the proposed structures, specially C-5 (spiro carbon) was found to resonate at about 95-90 ppm. This is similar to reported values of spiro carbon flanked by two nitrogen atoms in five-membered heterocycles, [2][3][4] which provide strong evidence in support of the structures 5a-l. The carbonyl carbon of the thiazolidinone ring appeared at about 170 ppm, the signal of the SCH 2 appeared at about 33-32 ppm and the signal at about 147 ppm, is attributed to C=N of the triazole ring.…”