Synthesis and selected properties of N substituted pyrrolo[2,1 c] 1,3 diazacycloalkano[1,2 a]pyrazinonesThe reactions of methyl α (2 formyl 1H pyrrol 1 yl)carboxylates with N substituted aliphatic 1,2 , 1,3 , and 1,4 diamines afford new pyrrole containing heterocyclic systems: 1,2,3,10b tetrahydroimidazo[1,2 a]pyrrolo[2,1 c]pyrazin 5(6H) ones, 1,3,4,11b tetrahydro 2H pyrrolo[2´,1´:3,4]pyrazino[1,2 a]pyrimidin 6(7H) ones, and 1,2,3,4,5,12b hexahydro pyrrolo[2´,1´:3,4]pyrazino[1,2 a][1,3]diazepin 7(8H) ones. The reduction of these compounds with different reagents was studied.* t 1 , 120-150 s; t 2 , 1 day; t 3 , 1 week. ** One isomer.
Scheme 6R´ = Me, n = 1 (a); R´ = H, n = 2 (b) which was obtained by subtraction of the spectrum recorded within one week after the dissolution of crystalline compound 1j in CDCl 3 from the spectrum recorded immediately after the dissolution (CDCl 3 ), δ: 1.79 (d, H, H a (CH b )Ar, 2 J = 13.3 Hz); 2.77 (ddd, 1 H, H a C(2), 2 J 2a,2b = 12.0 Hz, 3 J 2a,3b = 11.4 Hz, 3 J 2a,3a = 8.7 Hz); 2.89 (ddd, 1 H, H b C(2), 2 J 2b,2a = 12.0 Hz, 3 J 2b,3b =8.0 Hz, 3 J 2b,3a = 2.1 Hz); 2.99 (d, 1 H, H b (CH a )Ar, 2 J = 13.3 Hz); 3.33 (ddd, 1 H, H a C(3), 2 J 3a,3b = 11.5 Hz, 3 J 3a,2a = 8.7 Hz, 3 J 3a,2b = 2.1 Hz); 3.47 (dd, 1 H, H a (CH b )Ph, 2 J = 14.0 Hz, 3 J = 4.2 Hz); 3.55 (ddd, 1 H, H b C(3), 2 J 3b,3a = = 11.5 Hz, 3 J 3b,2a = 11.4 Hz, 3 J 3b,2b = 8.0 Hz); 3.68 (dd, H b (CH a )Ph, 2 J = 14.0 Hz, 3 J = 4.2 Hz); 3.84 and 3.86 (both s, 3 H each, 2 OMe); 5.04 (t, 1 H, CHCH 2 Ph, 3 J = 4.2 Hz); 5.20 (s, 1 H, H(10b)); 6.21 (m, 1 H, H(10)); 6.39 (m, 1 H, H(9)); 6.54 (d, 1 H, H Ar (5), 3 J = 8.1 Hz); 6.67 (m, 1 H, H(8)); 6.74 (d, 1 H, H Ar (6), 3 J = 8.1 Hz); 6.90-7.11 (m, 6 H, Ph, H Ar (2)). The 1 H NMR spectrum of the second diastereomer of 1j, which was obtained by subtraction of the spectrum recorded immediately after the dissolution of crystalline compound 1j in CDCl 3 from the spectrum recorded within one week after the dissolution (CDCl 3 ), δ: 2.39 (ddd, 1 H, H a C(2), 2 J 2a,2b = 10.9 Hz, 3 J 2a,3b = 11.1 Hz, 3 J 2a,3a = 8.5 Hz); 3.05 (ddd, 1 H, H b C(2), 2 J 2b,2a = 10.9 Hz, 3 J 2b,3b =7.6 Hz, 3 J 2b,3a = 1.9 Hz); 3.22-3.39 (m, 4 H, CH 2 Ph, H a (CH b )Ar, H a C(3)); 3.59 (ddd, 1 H, H b C(3), 2
