trans-cis-isomerization of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines on heating with triallylborane. Synthesis of (±)-dihydropinidine

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4631-4634

  Bubnov, Yuri N ^a   Klimkina, Elena V ^a   Ignatenko, Anatoly V ^a   Gridnev, Ilya D ^b  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; CIS TRANS ISOMERISM; DRUG SYNTHESIS; HEATING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030952437     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00953-2     Document Type: Article

References (21)

1. (a) Tawara, J. N.; Blokhin, A.; Federraro, T. A.; Stermitz, F. R.; Hope, H. J. Org. Chem. 1993, 58, 4813-4818 and references therein;
2. (b) Stermitz, F. R.; Tawara, J. N.; Boeckl, M.; Pomeroy, M.; Federraro, T. A.; Todd, F. G. Phytochemistry 1994, 35, 951-953;
3. (c) Tawara, J. N.; Stermitz, F. R.; Blokhin, A. V. Photochemistry 1995, 39, 705-709.
4. Brown, W. V.; Moore, B. P. Aust. J. Chem. 1982, 35, 1255-1261.
5. Attygalle, A. B.; Xu, S.-C.; McCormick, K. D.; Meinwald, J.; Blankespoor, C. L.; Eisner, T. Tetrahedron 1993, 49, 9333-9342.
6. (a) Ryckman, D. M.; Stevens, R. V. J. Org. Chem. 1987, 52, 4274-4279 and references;
7. (b) Comins, D. L.; Weglarz, M. A. J. Org. Chem. 1991, 56, 2506-2512;
8. (c) Yang, T.-K.; Teng, T.-F.; Lin, J.-H.; Lay, Y.-Y. Tetrahedron Lett. 1994, 35, 3581-3582 and references;
9. (d) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140.
10. (a) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608;
11. (b) Yamazaki, N.; Kibayashi, C. J. Am. Chem. Soc. 1989, 111, 1396-1408;
12. (c) Dolle, R. E.; Osifo, K. I.; Li, C.-S. Tetrahedron Lett. 1991, 32, 5029-5030;
13. (d) Lu, Z. H.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1993, 593-596;
14. (e) Chenevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341 and references therein.
15. (a) Bubnov, Yu. N. Pure Appl. Chem. 1994, 66, 235-244;
16. (b) Bubnov, Yu. N.; Shagova, E. A.; Evchenko, S. V.; Ignatenko, A. V. Izv. Akad. Nauk, Ser. Khim., 1994, 43, 693-704 [Russ. Chem. Bull. 1994, 43, 645 (Engl. Transl.)];
17. (b) Bubnov, Yu. N.; Shagova, E. A.; Evchenko, S. V.; Ignatenko, A. V. Izv. Akad. Nauk, Ser. Khim., 1994, 43, 693-704 [Russ. Chem. Bull. 1994, 43, 645 (Engl. Transl.)];
18. (c) Bubnov, Yu. N.; Shagova, E. A.; Evchenko, S. V.; Dekaprilevich, M. O.; Struchkov, Yu. T. Izv. Akad. Nauk, Ser. Khim. 1994, 43, 705-707 [Russ. Chem. Bull. 1994, 43, 657 (Engl. Transl.)].
19. (c) Bubnov, Yu. N.; Shagova, E. A.; Evchenko, S. V.; Dekaprilevich, M. O.; Struchkov, Yu. T. Izv. Akad. Nauk, Ser. Khim. 1994, 43, 705-707 [Russ. Chem. Bull. 1994, 43, 657 (Engl. Transl.)].
20. Bubnov, Yu. N.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1996, 37, 1317-1320.
21. 3J= 10.2 Hz), 6.0 (m, 1H, H-5), 7.23 (m, 3H, Ph), 7.59 (m, 2H, Ph), 9.25 (br.s, 2H, NH).