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5 3 ( 1, )2,5,6. 7. 1b [3,2 a] 4 ( 1, d)8. ( 9 1a.) , [3,2 a] (1) [3,2 a] (2) , 5. 5, 1b 2a . . 10 5a (R = Me) 5b (R = Ph) 4,5 2 , . 5a 10 , , ( 2). , 5a . a , 5a HClO4. 1 ( 5a) ( 7.8 ..) ( 5.70, 5.79 10.11 ..).

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2

3,6,7 [1,2 c] 1(2) (6). (, 11 [1,2 c] 1 .) , ANRORC ( 3). 5a . , 7 8 :
(7) = (5a) (ClO4) -- (2) + (OEt), (8) = (5a) (ClO4) -- (2) + (N(CH2)4)

13 .
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1 13 5a . 1 5.9 .., 5a ( 6.4--6.5 ..). , ( ) 5a . () . , , 1 ( ) [1,2 c] 7 8 ( 4). ( 12). 5a , 1 13 , 5a, . 13 2,3,5,7 [1,2 a] (9). , ( 5).

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X = NR2, RO

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5

, 5a , 5 [3,2 a] 5 , , 6--8. 5 2a 1b .
1 13 «Bruker AC 400» (1, 350 , 13, 100 ) d6. , -- SiMe4. «Kratos MS 30» (, 70 ). () Silufol F254 («Merck»); ( 254 365 ). 4,5 2 14. 2,3,5,7 [3,2 a] (5a) 4,5 2 10. 60%, .. 227--228 °C () (. .10: 227--228 °C). 1 (, ..): 2.59 (, 3 , (7)3); 2.72 (, 3 , (3)3); 2.77 (c, 3 H, (2)3); 3.06 (, 3 , (5)3); 7.80 (, 1 , (6)). 13, ..: 9.8; 10.0; 18.6; 24.3; 118.9; 121.3; 146.7; 153.1; 153.9; 172.4. 3,6,7 [1,2 c] 1(2 ) (6). 2.765 (0.01 ) 5a 100 20% NaOH 5 , 16 . , . 1.58 6. 90%, .. 179--181 °C. (%): , 67.93; , 6.88; N, 15.68. C10H12N2O. (%): , 68.16; , 6.86; N, 15.90. 1 (, ..): 1.99, 2.02 ( c, 3 H, (6)Me, C(7)Me); 2.55 (c, 3 H, C(3)H3); 5.70 (c, 1 H, H(5)); 5.79 (c, 1 H, H(4)); 10.11 (., 1 , NH). 13 (, ..): 10.9; 12.2; 17.6; 96.2; 102.5; 120.7; 121.4; 130.1; 130.7; 148.3. , m/z (I (%)): 176 [M]+ (100%). 3,6,7 1 [1,2 c] (7). 100 0.05 Na. 50 °C 2.765 (0.01 ) [3,2 a] 5a. 3 , , , . , . 1.63 (80%) 7, .. 38--40 °C. (%): , 70.04; , 7.60; N, 13.39. C10H12N2O. (%): , 70.56; , 7.89; N, 13.71.

1 (, ..): 1.45 (, 3 H, C(3)H3, J = 7.1 ); 2.10 (c, 3 H, C(7)H3); 2.17 (c, 3 H, C(6)H3); 2.56 (c, 3 H, C(3)H3); 4.49 (, 2 H, CH2, J = 7.1 ); 5.85 (c, 1 H, H(5)); 6.42 (, 1 H, H(4)). 13 (, ..): 11.5; 12.5; 14.0; 22.5; 63.2; 99.6; 103.7; 116.5; 122.5; 133.2; 138.0; 147.6. , m/z (I (%)): 204 [M]+ (54%), 175 (100). 1 () 3,6,7 [1,2 c] (8). 2.765 (0.01 ) 5a 50 , 50 °C, 0.05 4 . , , (3в20 ). Na2SO4 ; ( -- ), . 8 . 0.92 (40%). (%): , 73.22; , 8.37; N, 1 8.51. C14H19N 3. (%): , 73.33; , 8.35; N, 18.32. 1 (, ..): 1.91 (, 4 H, (CH2)2); 2.13 (c, 3 H, C(7)H3); 2.18 (c, 3 H, C(6)H3); 2.59 (c, 3 H, C(3)H3); 3.29 (, 4 H, N(CH2)2); 5.91 (c, 1 H, H(5)); 6.50 (, 1 H, H(4)). 13 (, ..): 11.5; 11.7; 22.4; 23.4; 50.2; 99.2; 104.9; 116.5; 123.8; 134.0; 137.4; 148.2. , m/z (I (%)): 229 [M]+ (100%). 2,3,5,7 [1,2 a] (9). 100 4 2.765 (0.01 ) 5a, 12 , 2 . , , . 1.5 9, 86%, .. 201--202 °C () (. .14: 202 °C). 1 (, ..): 2.23 (, 3 , (7)3); 2.38 (, 3 , (3)3); 2.61 (c, 3 H, (2)3); 2.80 (, 3 , (5)3); 6.58 (, 1 , (6)). 13 (, ..): 11.4; 13.1; 18.9; 23.7; 109.2; 115.1; 139.6; 144.8; 147.5; 157.1.

( 07 03 00921 05 03 39022 _).
1. . . , . . , . . , . . , . . . . . . ., 2005, 253 [Russ. Chem. Bull., Int. Ed., 2005, 54, 259]. 2. E. V. Babaev, A. V. Efimov, D. A. Maiboroda, and K. Jug, Eur. J. Org. Chem., 1998, 193. 3. . . , . . , . . , . . ., 1998, 32, 6, 24 [Pharm. Chem. J., 1998, 32, No. 6, 310 (Engl. Transl.)]. 4. V. L. Alifanov and E. V. Babaev, Synthesis, 2007, 263. 5. . . , . . , . . , . . , . , 1998, 34, 984 [Chem. He terocycl. Compd, 1998, 34, 852 (Engl. Transl.)].

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6. . . , . . . . , 1997, 33, 998 [Chem. Heterocycl. Compd., 1997, 33, 964 (Engl. Transl.)]. 7. P. Tielmann and C. Hoenke. Tetrahedron Lett ., 2006, 47, 261. 8. . . , . . , . ., . . , . , 1999, 35, 550 [Chem. He terocycl. Compd., 1999, 35, 486 (Engl. Transl.)]. 9. . . , . . , . . , . , 1997, 33, 397 [Chem. He terocycl. Compd., 1995, 33, 338 (Engl. Transl.)]. 10. . . в, . . . . . ., 1974, 40, 633 [Chem. Abstr., 1974, 81, 105438].

11. R. Buchan, M. Frazer, and C. Shand. J. Org. Chem., 1978, 43, 3544. 12. W. Flitsch, in Comprehensive Heterocyclic Chemistry, Eds A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, 4, 443. 13. P. Guerret, R. Jacquier, and G. Maury, Bull. Soc. Chim. France, 1972, 3503. 14. V. Wolf, P. Hauschildt, and W. Loop, Chem. Ber., 1962, 52, 2419.

20 2007; -- 5 2007