Facile KF/alumina mediated synthesis of α-heterosubstituted Weinreb amides

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 531-533

  Tius, Marcus A ^a   Busch Petersen, Jakob ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542638697     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6113     Document Type: Article

References (26)

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2. For a review, see: Sibi, M. P. Org. Prep. Proc. Intern. 1993, 25, 15.
3. For recent publications concerning classical/nonclassical cannabinoid hybrid analogs see: Tius, M. A.; Hill, W. A. G.; Zou, X.-L.; Busch-Petersen, J.; Kawakami, J. K.; Fernandez-Garcia, M. C.; Drake, D. J.; Abadji, V.; Makriyannis, A. Life Sci. 1995, 56, 2007 and references cited therein.
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5. 13C, IR, MS and HRMS data was obtained for this compound.
6. Graham, S. L.; Scholtz, T. H. Tetrahedron Lett. 1990, 31, 6268.
7. See also: Romo, D.; Johnson, D. D.; Plamondon, L.; Miwa, T.; Schreiber, S. L. J. Org. Chem. 1992, 57, 5060.
8. Tius, M. A.; Busch-Petersen, J. Unpublished results.
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11. 7a however, it was dried overnight at 250 °C (0.2 mmHg).
12. Ultrasound has previously been reported to enhance the reactivity of KCN/alumina: Ando, T.; Kawate, T.; Yamawaki, J.; Hanafusa, T. Chem. Lett. 1984, 725.
13. (a) Weinreb amides substituted at the α carbon by nitrogen: Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570.
14. Edwards, P. D.; Wolanin, D. J.; Andisik, D. W.; Davis, M. W. J. Med. Chem. 1995, 38, 76.
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17. (b) Weinreb amides substituted at the α carbon by oxygen: Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
18. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113.
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21. (c) Weinreb amides substituted at the α carbon by phosphorus: Netz, D. F.; Seidel, J. L. Tetrahedron Lett. 1992, 33, 1957. See also ref. 3.
22. (d) Weinreb amides substituted at the α carbon by sulfur: Selnick, H. G.; Radzilowski, E. M.; Ponticello, G. S. Tetrahedron Lett. 1991, 32, 721.
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24. 3CN in place of DMSO. Procedure A: same as procedure B, omitting sonication.)
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