Heterocyclic synthesis by C-C bond formation. Thionium ion-mediated preparation of substituted pyrrolidines and piperidines

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 147-150

  Craig, Donald ^a   Meadows, James D ^b   Pécheux, Muriel ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DITHIOACETAL 2,2 DIOXIDE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0031974052     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10472-5     Document Type: Article

References (16)

1. For an excellent account, see: Overman, L.E. Aldrichimica Acta 1995, 28, 107-120.
2. Craig D., Daniels K., MacKenzie A.R. Tetrahedron. 48:1992;7803-7816. and references cited therein.
3. Craig D., Pennington M.W., Warner P. Tetrahedron Lett. 36:1995;5815-5818.
4. Prepared using the Gabriel synthesis. See: Moody, C.J.; Rahimtoola, K.F.; Porter, B.; Ross, B.C. J. Org. Chem. 1992, 57, 2105-2114.
5. 13C nmr and ir spectra, and which showed low-resolution ms and either elemental combustion analysis or high-resolution ms characteristics in accord with the assigned structures.
6. For a review of the Pummerer reaction, see: Kennedy, M.; McKervey, M.A. in Comprehensive Organic Synthesis, eds. Trost, B.M.; Fleming, I.; Pergamon Press: New York, 1991, vol. 7 pp 193-216.
7. (4-Tolylsulfinyl)(4-tolylulfonyl)methane was prepared by addition of isopropyyl 4-tolylsulfinate to a mixture of lithiated (4-tolylsulfonyl)methane and t-BuOK followed by protonation.
8. (Methylsulfenyl)(4-tolylsulfonyl)methane was prepared from dimethylsulfoxide according to a published procedure: Ogura, K.; Yahata, N.; Watanabe, J.-I.; Takahashi, K.; Iida, H. Bull. Chem. Soc. Jpn. 1983, 56, 3543-3544.
9. N2-like reaction: Kataoka, T.; Tsutsumi, K.; Kano, K.; Mori, K.; Miyake, M.; Yokota, M.; Shimizu, H.; Hori, M. J. Chem. Soc., Perkin Trans. 1 1990, 3017-3025, and
10. (ii) by radical cyclisation: Ueno, Y.; Tanaka, C.; Okawara, M. Chem. Lett. 1983, 795-796.
11. Berry, M.B.; Craig, D. Synlett 1992, 41-44.
12. For studies on N-tosyl 2,6-dialkyl-2,6-dihydro-1H-pyridin-3-ones, see: Hopman, J.C.P.; van den Berg, E.; Ollero Ollero, L.; Hiemstra, H.; Speckamp, W.N. Tetrahedron Lett. 1995, 36, 4315-4318. For earlier work on the corresponding 3-hydroxy compounds, see: Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596.
13. For studies on N-tosyl 2,6-dialkyl-2,6-dihydro-1H-pyridin-3-ones, see: Hopman, J.C.P.; van den Berg, E.; Ollero Ollero, L.; Hiemstra, H.; Speckamp, W.N. Tetrahedron Lett. 1995, 36, 4315-4318. For earlier work on the corresponding 3-hydroxy compounds, see: Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596.
14. Brown J.D., Foley M.A., Comins D.L. J. Am. Chem. Soc. 110:1988;7445-7447.
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16. Rubiralta, M.; Giralt, E.; Diez, A., Piperidine: Structure, Preparation, Reactivity and Synthetic Applications of Piperidine and its Derivatives, Elsevier: New York, NY, 1991.