Synthesis of 2-azabicyclo[3.3.1]lnonanes by means of (carbamoyl)dichloromethyl radical cyclization

Tetrahedron

Volumn 53, Issue 4, 1997, Pages 1391-1402

  Quirante, Josefina ^a   Escolano, Carmen ^a   Massot, Mireia ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZABICYCLO[3.3.1]NONANE DERIVATIVE; BICYCLO[3.3.1]NONANE DERIVATIVE; UNCLASSIFIED DRUG;

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

EID: 0031038349     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01051-4     Document Type: Article

References (69)

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35. From radical addition to protected allylamines : Flynn, D. L.; Zabrowski, D. L. J. Org. Chem. 1990, 55, 3673-3674. Kataoka, T.; Yoshimatsu, M.; Noda, Y.; Sato, T.; Shimizu, H.; Hori, M. J. Chem. Soc. Perkin Trans 1, 1993, 121. Brumwell, J. E.; Simpkins, N. S.; Terrett, N. K. Tetrahedron 1994, 50, 13533-13552. Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. J. Chem. Soc., Perkin Trans 1, 1995, 19-26. Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
36. From radical addition to protected allylamines : Flynn, D. L.; Zabrowski, D. L. J. Org. Chem. 1990, 55, 3673-3674. Kataoka, T.; Yoshimatsu, M.; Noda, Y.; Sato, T.; Shimizu, H.; Hori, M. J. Chem. Soc. Perkin Trans 1, 1993, 121. Brumwell, J. E.; Simpkins, N. S.; Terrett, N. K. Tetrahedron 1994, 50, 13533-13552. Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. J. Chem. Soc., Perkin Trans 1, 1995, 19-26. Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
37. From radical addition to protected allylamines : Flynn, D. L.; Zabrowski, D. L. J. Org. Chem. 1990, 55, 3673-3674. Kataoka, T.; Yoshimatsu, M.; Noda, Y.; Sato, T.; Shimizu, H.; Hori, M. J. Chem. Soc. Perkin Trans 1, 1993, 121. Brumwell, J. E.; Simpkins, N. S.; Terrett, N. K. Tetrahedron 1994, 50, 13533-13552. Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. J. Chem. Soc., Perkin Trans 1, 1995, 19-26. Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
38. From radical addition to protected allylamines : Flynn, D. L.; Zabrowski, D. L. J. Org. Chem. 1990, 55, 3673-3674. Kataoka, T.; Yoshimatsu, M.; Noda, Y.; Sato, T.; Shimizu, H.; Hori, M. J. Chem. Soc. Perkin Trans 1, 1993, 121. Brumwell, J. E.; Simpkins, N. S.; Terrett, N. K. Tetrahedron 1994, 50, 13533-13552. Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. J. Chem. Soc., Perkin Trans 1, 1995, 19-26. Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
39. (a) Jasperse, G. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286.
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42. To our knowledge there are few precedents for the synthesis of six-membered rings from α-carbamoylmethyl radicals in a 6-exo radical process: see ref 9a and 15. See also ref 3.
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44. (b) Middleton, D. S.; Simpkins, N. S.; Terrett, N. K. Tetrahedron Lett. 1989, 30, 3865-3868.
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66. The reaction to elaborate this bridged azabicyclic nucleus from vinyl radicals in the amino series failed. A pyrrolidine ring is formed by a 1,5-hydrogen shift from the initially formed vinylic radical, followed by a 5-exo-trig cyclization of the resulting allylic radical: Lathbury, D. C.; Parsons, P. J.; Pinto, I. J. Chem. Soc., Chem. Commun. 1988, 81-82; Bonjoch, J.; Solé, D.; Bosch, J. J. Am. Chem. Soc. 1995, 117, 11017-11018. However, when the 1,5-hydrogen is not possible, the cyclization takes place: Kuehne, M. E.; Wang, T.; Seraphin, D. Synlett 1995, 557-558.
67. The reaction to elaborate this bridged azabicyclic nucleus from vinyl radicals in the amino series failed. A pyrrolidine ring is formed by a 1,5-hydrogen shift from the initially formed vinylic radical, followed by a 5-exo-trig cyclization of the resulting allylic radical: Lathbury, D. C.; Parsons, P. J.; Pinto, I. J. Chem. Soc., Chem. Commun. 1988, 81-82; Bonjoch, J.; Solé, D.; Bosch, J. J. Am. Chem. Soc. 1995, 117, 11017-11018. However, when the 1,5-hydrogen is not possible, the cyclization takes place: Kuehne, M. E.; Wang, T.; Seraphin, D. Synlett 1995, 557-558.
68. The reaction to elaborate this bridged azabicyclic nucleus from vinyl radicals in the amino series failed. A pyrrolidine ring is formed by a 1,5-hydrogen shift from the initially formed vinylic radical, followed by a 5-exo-trig cyclization of the resulting allylic radical: Lathbury, D. C.; Parsons, P. J.; Pinto, I. J. Chem. Soc., Chem. Commun. 1988, 81-82; Bonjoch, J.; Solé, D.; Bosch, J. J. Am. Chem. Soc. 1995, 117, 11017-11018. However, when the 1,5-hydrogen is not possible, the cyclization takes place: Kuehne, M. E.; Wang, T.; Seraphin, D. Synlett 1995, 557-558.
69. We have not observed an intramolecular ipso-attack of the radical derived from 19b or 20b on the aromatic ring such as occurs in some 3-benzyl-3-aza-5-hexenyl radicals or analogues: (a) Ishibashi, H.; Nakamura, N.; Ito, K.; Kitayama, S.; Ikeda, M. Heterocycles 1990, 31, 1781-1784. (b) ref 9b.