A direct entry to substituted piperidinones from α, β-unsaturated amides by means of aza double Michael reaction

Tetrahedron Letters

Volumn 44, Issue 40, 2003, Pages 7429-7432

  Takasu, Kiyosei ^a   Nishida, Naoko ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

1,4 additions; Anti depressant; Domino reactions; Heterocycles; Piperidines; Unsaturated amides

Indexed keywords

AMIDE; PAROXETINE; PIPERIDINE DERIVATIVE; PIPERIDONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; CONCENTRATION RESPONSE; DRUG SYNTHESIS; MICHAEL ADDITION;

EID: 0041834590     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.025     Document Type: Article

References (21)

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5. Annulation reaction of α,β-unsaturated imines, which are mono-reduced derivatives of α,β-unsaturated amides, are well investigated: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987; pp. 240-255; (b) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379-471; (c) Wei, L.-L.; Hsung, R. P.; Sklenicka, H. M.; Gerasyuto, A. I. Angew. Chem., Int. Ed. 2001, 40, 1516-1518.
6. Annulation reaction of α,β-unsaturated imines, which are mono-reduced derivatives of α,β-unsaturated amides, are well investigated: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987; pp. 240-255; (b) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379-471; (c) Wei, L.-L.; Hsung, R. P.; Sklenicka, H. M.; Gerasyuto, A. I. Angew. Chem., Int. Ed. 2001, 40, 1516-1518.
7. Annulation reaction of α,β-unsaturated imines, which are mono-reduced derivatives of α,β-unsaturated amides, are well investigated: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987; pp. 240-255; (b) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379-471; (c) Wei, L.-L.; Hsung, R. P.; Sklenicka, H. M.; Gerasyuto, A. I. Angew. Chem., Int. Ed. 2001, 40, 1516-1518.
8. To the best of our knowledge, only limited examples were reported for the synthesis of piperidines by means of cyclodimerization of acrylamide equivalents: (a) Lorente, A.; Navio, J. L. G.; Perez, J. C. L.; Soto, J. L. Synthesis 1985, 89-92; (b) Elliott, M. C.; Galea, N. M.; Long, M. S.; Willock, D. J. Tetrahedron Lett. 2001, 42, 4937-4939.
9. To the best of our knowledge, only limited examples were reported for the synthesis of piperidines by means of cyclodimerization of acrylamide equivalents: (a) Lorente, A.; Navio, J. L. G.; Perez, J. C. L.; Soto, J. L. Synthesis 1985, 89-92; (b) Elliott, M. C.; Galea, N. M.; Long, M. S.; Willock, D. J. Tetrahedron Lett. 2001, 42, 4937-4939.
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14. 3SiX sometimes give different results (for 3a ; 60-80% yield), whereas use of freshly distilled TBSOTf with tBuOH (0.25 equiv.) affords highly reproducible results. We have reported purity of TMSI affects on the chemical yield on intramolecular Michael-aldol reaction. Takasu, K.; Ueno, M.; Ihara, M. J. Org. Chem. 2001, 66, 4667-4672.
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16. Recent examples for the synthesis of paroxetine, see: (a) Greenhalgh, D. A.; Simpkins, N. S. Synlett 2002, 2074-2076; (b) Senda, T.; Ogasawara, M. Hayashi, T. J. Org. Chem. 2001, 66, 6852-6856; (c) Cossy, J.; Mirguet, O.; Pardo, D. G.; Desmurs, J.-R. Eur. J. Org. Chem. 2002, 3543-3551 and references cited therein; (d) Yu, M. S.; Lantos, I.; Peng, Z.-Q.; Yu, J.; Cacchio, T. Tetrahedron Lett. 2000, 41, 5647-5651; (e) Murthy, K. S. K.; Rey, A. W.; Tjepkema, M. Tetrahedron Lett. 2003, 44, 5355-5358.
17. Recent examples for the synthesis of paroxetine, see: (a) Greenhalgh, D. A.; Simpkins, N. S. Synlett 2002, 2074-2076; (b) Senda, T.; Ogasawara, M. Hayashi, T. J. Org. Chem. 2001, 66, 6852-6856; (c) Cossy, J.; Mirguet, O.; Pardo, D. G.; Desmurs, J.-R. Eur. J. Org. Chem. 2002, 3543-3551 and references cited therein; (d) Yu, M. S.; Lantos, I.; Peng, Z.-Q.; Yu, J.; Cacchio, T. Tetrahedron Lett. 2000, 41, 5647-5651; (e) Murthy, K. S. K.; Rey, A. W.; Tjepkema, M. Tetrahedron Lett. 2003, 44, 5355-5358.
18. Recent examples for the synthesis of paroxetine, see: (a) Greenhalgh, D. A.; Simpkins, N. S. Synlett 2002, 2074-2076; (b) Senda, T.; Ogasawara, M. Hayashi, T. J. Org. Chem. 2001, 66, 6852-6856; (c) Cossy, J.; Mirguet, O.; Pardo, D. G.; Desmurs, J.-R. Eur. J. Org. Chem. 2002, 3543-3551 and references cited therein; (d) Yu, M. S.; Lantos, I.; Peng, Z.-Q.; Yu, J.; Cacchio, T. Tetrahedron Lett. 2000, 41, 5647-5651; (e) Murthy, K. S. K.; Rey, A. W.; Tjepkema, M. Tetrahedron Lett. 2003, 44, 5355-5358.
19. Recent examples for the synthesis of paroxetine, see: (a) Greenhalgh, D. A.; Simpkins, N. S. Synlett 2002, 2074-2076; (b) Senda, T.; Ogasawara, M. Hayashi, T. J. Org. Chem. 2001, 66, 6852-6856; (c) Cossy, J.; Mirguet, O.; Pardo, D. G.; Desmurs, J.-R. Eur. J. Org. Chem. 2002, 3543-3551 and references cited therein; (d) Yu, M. S.; Lantos, I.; Peng, Z.-Q.; Yu, J.; Cacchio, T. Tetrahedron Lett. 2000, 41, 5647-5651; (e) Murthy, K. S. K.; Rey, A. W.; Tjepkema, M. Tetrahedron Lett. 2003, 44, 5355-5358.
20. Recent examples for the synthesis of paroxetine, see: (a) Greenhalgh, D. A.; Simpkins, N. S. Synlett 2002, 2074-2076; (b) Senda, T.; Ogasawara, M. Hayashi, T. J. Org. Chem. 2001, 66, 6852-6856; (c) Cossy, J.; Mirguet, O.; Pardo, D. G.; Desmurs, J.-R. Eur. J. Org. Chem. 2002, 3543-3551 and references cited therein; (d) Yu, M. S.; Lantos, I.; Peng, Z.-Q.; Yu, J.; Cacchio, T. Tetrahedron Lett. 2000, 41, 5647-5651; (e) Murthy, K. S. K.; Rey, A. W.; Tjepkema, M. Tetrahedron Lett. 2003, 44, 5355-5358.
21. In this sequence, cis-3c was obtained in 14% yield along with trans-3c . cis-3c can be converted into trans-3c by treatment with NaOMe.