Generation and trapping of tricyclo[3.3.0.03,7]oct-1(5)-ene derivatives containing carbonyl functionalities

Synthesis and thermal transformations of pyrazolines obtained by 1,3-dipolar addition of diazocyclopropane to maleimides

“…1.08 (m, 4 H, CH 2 CH 2 ); 1.96 (m, 1 H, CH); 6.14 (s, 1 H, =CH); 7.20-7.50 (m, Ph). 13 C NMR (CDCl 3 ), δ: 8.4 (CH); 12.0 (CH 2 CH 2 ); 120.7 (C(4)); 126.0 (o C); 127.6 (p C); 128.6 (m C); 131.6 (ipso C); 153.5 C(3); 169.2, 169.7 (2 CO).…”

“…According to the 1 H NMR spectrum, the residue was a mixture of starting compound 3a and isomeric pyrazolines 6 and 7 in the molar ratio ~3.8 : 1.7 : 1, respectively. Individual pyrazoline 6 (72 mg, 60%) was 13 C NMR (CDCl 3 ), δ: 1.3, 1.4 (CH 2 CH 2 ); 11.4, 16.7 (C(2´) and C(3´)); 13.2 (CH); 44.2 (C(5)); 72.9 (C(4)); 101.9 (C(1)); 126.3 (o C); 129.0 (p C); 129.3 (m C); 131.0 (ipso C); 171.2, 173.1 (2 CO). The filtrate left after isolation of pyrazoline 6 was concentrated and the residue was separated by TLC on silica gel (eluent, ether) to obtain pyrazoline 7 (0.026 g, 22%) as yellowish fusible crystals, R f = 0.74.…”

“…144-146 °C. Partial MS (EI), m/z (I rel (%)): 237 (3) 13 C NMR (CDCl 3 ), δ: 5.4, 8.6 (C(4) and C(5)); 23.9 (C(3)); 24.8 (2 CH 2 ); 25.4 (CH 2 ); 29.0, 30.7 (C(1) and C(2)); 32.6, 32.7 (2 CH 2 ); 49.7 (NCH); 172.4, 173.5 (2 CO).…”

“…1 1) and H(2), 3 J = 8.0 Hz); 3.73 (s, 3 H, OMe); 3.75 (m, 1 H, NCH); 6.59 (s, 1 H, NH). 13 C NMR (CDCl 3 ), δ: 4.9, 7.9 (C(4) and C(5)); 21.4 (C(3)); 24.6, 25.6 (CH 2 cyclohexyl ); 26.5, 30.9 (C(1) and C(2)); 29.1, 32.7, 33.1 (CH 2 cyclohexyl ); 48.0 (NCH); 52.1 (OMe); 168.1 (COO); 172.0 (CONH).…”

“…Experimental1 H and13 C NMR spectra were recorded on a Bruker AC 200 (200 and 50.3 MHz) and Bruker AM 300 spectrometers (300 and 75.5 MHz, respectively) for solutions in CDCl 3 or (CD 3 ) as the internal standard. Mass spectra were recorded on a Finnigan MAT INCOS 50 instrument (EI, 70 eV, direct inlet).…”