3a-(o-nitrophenyl)octahydroindol-4-ones: Synthesis and spectroscopic analysis

Tetrahedron

Volumn 52, Issue 11, 1996, Pages 4013-4028

  Solé, Daniel ^a   Bosch, Joan ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029962138     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00065-8     Document Type: Article

References (62)

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2. For a review, see: Bosch, J.; Bonjoch, J.; Amat, M. in "The Alkaloids", vol. 48, Cordell, G. A., ed.; Academic Press: New York, in press. For the use of octahydroindolone cis-1a in the total synthesis of Strychnos alkaloids, see: Bonjoch, J.; Solé, D.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 3030-3031.
3. For a review, see: Bosch, J.; Bonjoch, J.; Amat, M. in "The Alkaloids", vol. 48, Cordell, G. A., ed.; Academic Press: New York, in press. For the use of octahydroindolone cis-1a in the total synthesis of Strychnos alkaloids, see: Bonjoch, J.; Solé, D.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 3030-3031.
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23. 3) yields. The use of NaH, DBU or Triton B as a bases induces decomposition of dione. In some runs, the reaction was conducted in DMF with a similar results, but when using acetone the starting material was recovered.
24. For recent studies in the mechanism of this nitroarylation type, see: Zhang, X.-M.; Yang, D.-L.; Liu, Y.-C. J. Org. Chem. 1993, 58, 224-227.
25. 4) were unsuccessful.
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29. Although the reductive amination has been extensively utilized, there are limited examples involving the formation of cyclic amines from a dicarbonyl compounds and an amine; (a) pyrrolidines: Jones, T. H.; Franko, J. B.; Blum, M. S.; Fales, H. M. Tetrahedron Lett. 1980, 21, 789-792; Boga, C.; Manescalchi, F.; Savoia, D. Tetrahedron 1994, 50, 4709-4722.
30. Although the reductive amination has been extensively utilized, there are limited examples involving the formation of cyclic amines from a dicarbonyl compounds and an amine; (a) pyrrolidines: Jones, T. H.; Franko, J. B.; Blum, M. S.; Fales, H. M. Tetrahedron Lett. 1980, 21, 789-792; Boga, C.; Manescalchi, F.; Savoia, D. Tetrahedron 1994, 50, 4709-4722.
31. (b) piperidines: Abe, K.; Okumura, H.; Tsugoshi, T.; Nakamura, N. Synthesis 1984, 597-598; Kawaguchi, M.; Hayashi, O.; Sakai, N.; Hamada, M.; Yamamoto, Y.; Oda, J. Agric. Biol. Chem, 1986, 50, 3107-3112; Ryckman, D. M.; Stevens, R. V. J. Org. Chem. 1987, 52, 4274-4279; Hanessian, S.; Faucher, A.-M. Léger, S. Tetrahedron 1990,46, 231-243; Hirst, G. C.; Johnson, Jr., T. O.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 2992-2993; Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185.
32. (b) piperidines: Abe, K.; Okumura, H.; Tsugoshi, T.; Nakamura, N. Synthesis 1984, 597-598; Kawaguchi, M.; Hayashi, O.; Sakai, N.; Hamada, M.; Yamamoto, Y.; Oda, J. Agric. Biol. Chem, 1986, 50, 3107-3112; Ryckman, D. M.; Stevens, R. V. J. Org. Chem. 1987, 52, 4274-4279; Hanessian, S.; Faucher, A.-M. Léger, S. Tetrahedron 1990,46, 231-243; Hirst, G. C.; Johnson, Jr., T. O.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 2992-2993; Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185.
33. (b) piperidines: Abe, K.; Okumura, H.; Tsugoshi, T.; Nakamura, N. Synthesis 1984, 597-598; Kawaguchi, M.; Hayashi, O.; Sakai, N.; Hamada, M.; Yamamoto, Y.; Oda, J. Agric. Biol. Chem, 1986, 50, 3107-3112; Ryckman, D. M.; Stevens, R. V. J. Org. Chem. 1987, 52, 4274-4279; Hanessian, S.; Faucher, A.-M. Léger, S. Tetrahedron 1990,46, 231-243; Hirst, G. C.; Johnson, Jr., T. O.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 2992-2993; Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185.
34. (b) piperidines: Abe, K.; Okumura, H.; Tsugoshi, T.; Nakamura, N. Synthesis 1984, 597-598; Kawaguchi, M.; Hayashi, O.; Sakai, N.; Hamada, M.; Yamamoto, Y.; Oda, J. Agric. Biol. Chem, 1986, 50, 3107-3112; Ryckman, D. M.; Stevens, R. V. J. Org. Chem. 1987, 52, 4274-4279; Hanessian, S.; Faucher, A.-M. Léger, S. Tetrahedron 1990,46, 231-243; Hirst, G. C.; Johnson, Jr., T. O.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 2992-2993; Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185.
35. (b) piperidines: Abe, K.; Okumura, H.; Tsugoshi, T.; Nakamura, N. Synthesis 1984, 597-598; Kawaguchi, M.; Hayashi, O.; Sakai, N.; Hamada, M.; Yamamoto, Y.; Oda, J. Agric. Biol. Chem, 1986, 50, 3107-3112; Ryckman, D. M.; Stevens, R. V. J. Org. Chem. 1987, 52, 4274-4279; Hanessian, S.; Faucher, A.-M. Léger, S. Tetrahedron 1990,46, 231-243; Hirst, G. C.; Johnson, Jr., T. O.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 2992-2993; Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185.
36. (b) piperidines: Abe, K.; Okumura, H.; Tsugoshi, T.; Nakamura, N. Synthesis 1984, 597-598; Kawaguchi, M.; Hayashi, O.; Sakai, N.; Hamada, M.; Yamamoto, Y.; Oda, J. Agric. Biol. Chem, 1986, 50, 3107-3112; Ryckman, D. M.; Stevens, R. V. J. Org. Chem. 1987, 52, 4274-4279; Hanessian, S.; Faucher, A.-M. Léger, S. Tetrahedron 1990,46, 231-243; Hirst, G. C.; Johnson, Jr., T. O.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 2992-2993; Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185.
37. (c) perhydroquinolines: Abe, K.; Tsugoshi, T.; Nakamura, N. Bull. Chem. Soc. Jpn. 1984, 57, 3351-3352.
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40. Compound 9 was reluctant to condense with an amino group in an intermolecular manner; neither reductive amination with ethyl glycinate hydrochloride nor imine formation with benzylamine took place, the starting material being recovered.
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56. The 3a-unsubstituted octahydroindoles also show a conformation with the alkylamino group equatorially located with respect to the carbocyclic ring, inter alia: Wenkert, D.; Ferguson, S. B.; Porter, B.; Qvarnstrom, A.; McPhail, A. T. J. Org. Chem. 1985, 50, 4114-4119; Bäckvall, J.-E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988-2993.
57. The 3a-unsubstituted octahydroindoles also show a conformation with the alkylamino group equatorially located with respect to the carbocyclic ring, inter alia: Wenkert, D.; Ferguson, S. B.; Porter, B.; Qvarnstrom, A.; McPhail, A. T. J. Org. Chem. 1985, 50, 4114-4119; Bäckvall, J.-E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988-2993.
58. Compare the values of the benzhydridyl derivatives cis-1e (δ 47.1 and 66.1 for C-2 and C-7a) and the analogue 3a-phenyl substituted in reference 8 (δ 43.8 and 64.9 for the sames carbons)
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62. Bringmann, G.; Geisler, J.-P. Synthesis 1989, 608-610.