Free radical method for the synthesis of spiro-piperidinyl heterocycles

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5233-5234

  Chen, Meng Hsin ^a   Abraham, John A ^a,b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030598001     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01072-6     Document Type: Article

References (14)

1. 1) Patchett, A. A.; Nargund, R. P.; Tata, J. R.; Chen, M.-H.; Barakat, K. J.; Johnston, D. B. R.; Cheng, K. Chan, W. W.-S.; Butler, B.; Hickey, G.; Jacks, T.; Schleim, K.; Pong, S.-S.; Chaung, L.-Y. P.; Chen, H. Y.; Frazier, E.; Leung, K. H.; Chiu, S.-H. L. and Smith, R. G. Proc. Natl. Acad. Sci. 1995, 92, 7001.
2. 2) For a review see: Curran, D. P. in Comprehensive Organic Synthesis Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991, Vol. 4, 715 and 779.
3. 3) Beckwith A. L. J. and Gara, W. B., J. Chem. Soc., Perkin Trans. 2, 1975, 593, 795.; Beckwith A. L. J. and Meijs, G. F. J. Chem. Soc., Chem. Comm. 1981, 136.
4. 3) Beckwith A. L. J. and Gara, W. B., J. Chem. Soc., Perkin Trans. 2, 1975, 593, 795.; Beckwith A. L. J. and Meijs, G. F. J. Chem. Soc., Chem. Comm. 1981, 136.
5. 4) For spiro heteocycles formation see: Cheng, C.-Y.; Liou, J.-P. and Wei, H.-L. The 15th International Congress of Heterocyclic Chemistry, Aug. 6-11, 1995, Taipei, Taiwan. Jones, K. J. Chem. Soc., Chem. Comm. 1986, 115. For benzo-fused heterocycles formation see: Sloan, C. P.; Cuevas, J. C.; Quesnelle, C. and Snieckus, V. Tetrahedron Lett 1988, 29, 4685. Wolff, S. and Hoffman, H. M. R. Synthesis 1988, 760. Boger, D. L. and Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 4796.
6. 4) For spiro heteocycles formation see: Cheng, C.-Y.; Liou, J.-P. and Wei, H.-L. The 15th International Congress of Heterocyclic Chemistry, Aug. 6-11, 1995, Taipei, Taiwan. Jones, K. J. Chem. Soc., Chem. Comm. 1986, 115. For benzo-fused heterocycles formation see: Sloan, C. P.; Cuevas, J. C.; Quesnelle, C. and Snieckus, V. Tetrahedron Lett 1988, 29, 4685. Wolff, S. and Hoffman, H. M. R. Synthesis 1988, 760. Boger, D. L. and Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 4796.
7. 4) For spiro heteocycles formation see: Cheng, C.-Y.; Liou, J.-P. and Wei, H.-L. The 15th International Congress of Heterocyclic Chemistry, Aug. 6-11, 1995, Taipei, Taiwan. Jones, K. J. Chem. Soc., Chem. Comm. 1986, 115. For benzo-fused heterocycles formation see: Sloan, C. P.; Cuevas, J. C.; Quesnelle, C. and Snieckus, V. Tetrahedron Lett 1988, 29, 4685. Wolff, S. and Hoffman, H. M. R. Synthesis 1988, 760. Boger, D. L. and Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 4796.
8. 4) For spiro heteocycles formation see: Cheng, C.-Y.; Liou, J.-P. and Wei, H.-L. The 15th International Congress of Heterocyclic Chemistry, Aug. 6-11, 1995, Taipei, Taiwan. Jones, K. J. Chem. Soc., Chem. Comm. 1986, 115. For benzo-fused heterocycles formation see: Sloan, C. P.; Cuevas, J. C.; Quesnelle, C. and Snieckus, V. Tetrahedron Lett 1988, 29, 4685. Wolff, S. and Hoffman, H. M. R. Synthesis 1988, 760. Boger, D. L. and Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 4796.
9. 4) For spiro heteocycles formation see: Cheng, C.-Y.; Liou, J.-P. and Wei, H.-L. The 15th International Congress of Heterocyclic Chemistry, Aug. 6-11, 1995, Taipei, Taiwan. Jones, K. J. Chem. Soc., Chem. Comm. 1986, 115. For benzo-fused heterocycles formation see: Sloan, C. P.; Cuevas, J. C.; Quesnelle, C. and Snieckus, V. Tetrahedron Lett 1988, 29, 4685. Wolff, S. and Hoffman, H. M. R. Synthesis 1988, 760. Boger, D. L. and Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 4796.
10. 5) Shirahama, H. Chem. Lett. 1981, 1703.
11. 3SnH, 1.5 eq; AIBN, cat. amount; 0.02N/benzene, 100°C; 12 h.
12. 3): 7.18 (d, 7 Hz, 1H), 7.12 (td, 7, 2 Hz, 1H), 7.04 (m, 2H), 4.10 (br s, 2H), 3.30 (s, 2H), 2.87 (m, 2H), 1.79 (br s, 4H), 1.46 (s, 9H).
13. 3): 7.22 (m, 1H), 7.05 (m, 3H), 3.87 (m, 1H), 3.71 (dt, 14, 5 Hz, 1H), 3.39 (m, 1H), 3.27 (t, 12 Hz, 1H), 3.14 (br t, 14 Hz, 1H), 2.95 (dt, 10, 4 Hz, 1H), 2.75 (m, 1H), 2.43 (m, 1H), 1.88 (m, 1H), 1.70 (m, 1H), 1.46 (s, 9H). The cis stereochemistry was confirmed both by NOE observation and the coupling constant of the junction protons.
14. 9) Curran, D. P. and Chang, C.-T. J. Org. Chem. 1989, 54, 3140.