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Volumn 65, Issue 14, 2000, Pages 4397-4408

New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building-blocks

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; INDOLE DERIVATIVE; LACTAM DERIVATIVE; OXAZOLINE DERIVATIVE; PHENOL DERIVATIVE; SPIRO COMPOUND; SPIRONOLACTONE;

EID: 0034647499     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000341v     Document Type: Article
Times cited : (123)

References (58)
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    • E.g., FR901483: (a) Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara M. J. Antibiot. 1996, 49, 37 (isolation). (b) Snider, B. B.; Lin, H.; Foxman, B. M. J. Am. Chem. Soc. 1999, 121, 7778 (synthesis). TAN-1251: (c) Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. World Patent WO 91/13887 (1991) to Takeda Chemical Industries, Ltd. (isolation). (d) Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Kawahara, N. Tetrahedron Lett. 1998, 39, 4493 (synthesis). Cyclindricines: (e) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. H. Tetrahedron 1993, 49, 8645 (isolation). (f) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183 (synthesis).
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    • Alternative methods for the preparation of related spiroheterocycles: (a) Bryce, M. R.; Gardiner, J. M.; Horton, P. J.; Smith, S. A. J. Chem. Res., Synop. 1989, 1. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 5985. (c) Cossy, J.; Bouzide, A. Tetrahedron 1997, 53, 5775.
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    • Alternative methods for the preparation of related spiroheterocycles: (a) Bryce, M. R.; Gardiner, J. M.; Horton, P. J.; Smith, S. A. J. Chem. Res., Synop. 1989, 1. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 5985. (c) Cossy, J.; Bouzide, A. Tetrahedron 1997, 53, 5775.
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    • Alternative methods for the preparation of related spiroheterocycles: (a) Bryce, M. R.; Gardiner, J. M.; Horton, P. J.; Smith, S. A. J. Chem. Res., Synop. 1989, 1. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 5985. (c) Cossy, J.; Bouzide, A. Tetrahedron 1997, 53, 5775.
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    • note
    • It may also be surmised that adventitious moisture might have promoted hydolysis of the imino ether, resulting in liberation of MeOH. However, it is not likely that the reaction medium contained enough water to permit formation of 27-29 in the observed yields. In addition, products of hydroxylation of the substrate (cf. 25/26, Z = H) would also have resulted if sufficient moisture were present in the system, as it happens indeed when similar phenols of the type are exposed to DIB in moist trifloroethanol.
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    • All computational work described herein was carried out with the PC-based Hyperchem package, available from Hypercube, Inc., Ontario, Canada.
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    • Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, UK, (Sutherland, I. O., Ed.), Chapter 8. See especially pp 396-7 and references therein
    • Cf., e.g.: (a) Lambert, J. B.; Takeuchi, Y. Cyclic Organonitrogen Stereodynamics; VCH: New York, NY, 1992; pp 76 ff. (b) Tennant, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, UK, 1979; Vol. 2 (Sutherland, I. O., Ed.), Chapter 8, pp 385-590. See especially pp 396-7 and references therein.
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    • Cf., e.g.: (a) Chow, Y. L.; Colón, C. J.; Tan, J. N. S. Can. J. Chem. 1968, 46, 2821. (b) Lunazzi, L.; Cerioni, G.; Foresti, E.; Macciantelli, D. J. Chem. Soc., Perkin Trans. 2 1980, 717 . See also: Johnson, F. Chem. Rev. 1968, 68, 375.
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    • note
    • (a) Calculated by molecular mechanics (MM+). This probably represent a lower limit for this value, since the MM+ force field tends to underestimate DE's for conformers of highly strained systems such as the ones discussed herein. (b) Approximate transition state structures were created by fixing the distance between the reacting atoms at 2.5 Å and by allowing the remainder of the molecular framework to relax in the MM+ force field.
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    • Implicit in this surmise was the assumption that the reversibility of the conjugate addition of the OH group to the dienone would probably lead to a thermodynamic product.
  • 37
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    • Some degradation of the substrate became evident after 12 h of exposure to the Dess-Martin oxidant.
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    • For related quinonimine syntheses see ref 10 as well as: (a) Barret, R.; Daudon, M. Tetrahedron Lett. 1991, 32, 2133-2134. (b) Kita, Y.; Egi, M.; Okajima, A.; Ohtsubo, M.; Takada, T.; Tohma, H. Chem. Commun. 1996, 1491-1492. (c) Related spirocycles formally derived from indoles: Rodriguez, J. G.; Urrutia, A.; de Diego, J. E.; Martinez-Alcazar, M. P.; Fonseca, I. J. Org. Chem. 1998, 63, 4332- 4337.
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    • For related quinonimine syntheses see ref 10 as well as: (a) Barret, R.; Daudon, M. Tetrahedron Lett. 1991, 32, 2133-2134. (b) Kita, Y.; Egi, M.; Okajima, A.; Ohtsubo, M.; Takada, T.; Tohma, H. Chem. Commun. 1996, 1491-1492. (c) Related spirocycles formally derived from indoles: Rodriguez, J. G.; Urrutia, A.; de Diego, J. E.; Martinez-Alcazar, M. P.; Fonseca, I. J. Org. Chem. 1998, 63, 4332- 4337.
    • (1996) Chem. Commun. , pp. 1491-1492
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  • 45
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    • For related quinonimine syntheses see ref 10 as well as: (a) Barret, R.; Daudon, M. Tetrahedron Lett. 1991, 32, 2133-2134. (b) Kita, Y.; Egi, M.; Okajima, A.; Ohtsubo, M.; Takada, T.; Tohma, H. Chem. Commun. 1996, 1491-1492. (c) Related spirocycles formally derived from indoles: Rodriguez, J. G.; Urrutia, A.; de Diego, J. E.; Martinez-Alcazar, M. P.; Fonseca, I. J. Org. Chem. 1998, 63, 4332-4337.
    • (1998) J. Org. Chem. , vol.63 , pp. 4332-4337
    • Rodriguez, J.G.1    Urrutia, A.2    De Diego, J.E.3    Martinez-Alcazar, M.P.4    Fonseca, I.5
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