?-hydroaxyalkyl(benzyl)furozans and ?-hydroxyalkyl(benzyl)furoxans synthesis and reactivity

Synthesis of 4-Acyl-3-Aminofurazans from 3,4-Diacylfuroxans

“…At the same time, the synthetic potential of synthons with ortho-lockated amine and acyl groups is quite substantial and opens the possibilities for construction of diverse fused heterocycles [2-6]. On the other hand, involving one of these functionalities in a reaction provides access to polyfunctional compounds [7][8][9][10][11][12][13][14][15][16][17][18][19].…”

“…At the same time, the synthetic potential of synthons with ortho-lockated amine and acyl groups is quite substantial and opens the possibilities for construction of diverse fused heterocycles [2-6]. On the other hand, involving one of these functionalities in a reaction provides access to polyfunctional compounds [7][8][9][10][11][12][13][14][15][16][17][18][19].A study of 3,4-di(4-methylbenzoyl)furoxan (1а) reaction with aqueous ammonia (Scheme 1) was published in 1887, and the reported product had the empirical formula of C 10 H 9 N 3 O 2 . This compound was tentatively identified as 3-amino-4-(4-methylbenzoyl)furazan (2а) [20,21]; methylbenzoyl amide was formed as by-product.…”

Novel synthesis of 3-monosubstituted furoxans

“…Recently, 1 we have proposed a general preparative synthesis of α-hydroxyalkyl(benzyl)furoxan and -furazan derivatives based on the reduction of acyl and ethoxycarbonyl substituents in these heterocycles with NaBH 4 in EtOH. Acyl, methyl and amino groups were second substituents in the compounds studied.…”

“…IR spectra were recorded in KBr pellets. 1 H, 13 C and 15 N NMR spectra (300, 75.5 and 30.4 MHz, respectively) were measured in CDCl 3 , internal standard SiMe 4 for 1 H and 13 C and external standard MeNO 2 for 15 N.…”

“…3-Ethoxycarbonylfuroxan 4: yield 53%, high-boiling liquid, R f 0.62 (CHCl 3 ). 1 H NMR, d: 1.20 (t, 3H, Me, 3 J 7.7 Hz), 4.17 (q, 2H, CH 2 , 3 J 7.7 Hz), 8.20 (s, 1H, CH). 13 13 C NMR, d: 8.16 (dq, Me, 1 J 132 Hz, 3 J 6.0 Hz), 113.45 (m, C-3 in furoxan ring, 2 J 6.0 Hz), 148.25 (dt, C-4 in furoxan ring, 1 J 200 Hz, 3 J 3.2 Hz).…”