Pictet-Spengler condensation of N-sulfonyl-β-phenethylamines with α- chloro-α-phenylselenoesters. New synthesis of 1,2,3,4- tetrahydroisoquinoline-1-carboxylates

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 4969-4972

  Silveira, Claudio C ^a   Bernardi, Carmem R ^a   Braga, Antonio L ^a   Kaufman, Teodoro S ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROISOQUINOLINE 1 CARBOXYLIC ACID DERIVATIVE; CALYCOTOMINE; CARBOXYLIC ACID DERIVATIVE; ISOQUINOLINE DERIVATIVE; N SULFONYL BETA PHENETHYLAMINE DERIVATIVE; PHENETHYLAMINE DERIVATIVE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; POLYMERIZATION; REACTION ANALYSIS;

EID: 0033516633     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00958-2     Document Type: Article

References (26)

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2. For reviews, see: a) Whaley, W. M.; Govindachari, T. R Org. React. 1951, 6, 151; b) Kametani, T.; Fukumoto, K. in The Chemistry of Heterocyclic Compounds, Isoquinolines Part One; Ed.: Grethe, G.; Wiley, N.Y. 1981; pp 170-182; c) Jones, G. in Comprehensive Heterocyclic Chemistry, Eds.: Katritzky, A. R.; Rees, C. W.; Pergamon, Oxford, 1984; Vol. 2, pp 438-440.
3. For reviews, see: a) Whaley, W. M.; Govindachari, T. R Org. React. 1951, 6, 151; b) Kametani, T.; Fukumoto, K. in The Chemistry of Heterocyclic Compounds, Isoquinolines Part One; Ed.: Grethe, G.; Wiley, N.Y. 1981; pp 170-182; c) Jones, G. in Comprehensive Heterocyclic Chemistry, Eds.: Katritzky, A. R.; Rees, C. W.; Pergamon, Oxford, 1984; Vol. 2, pp 438-440.
4. a) Lazarus, S.; Wittekind, R. R. J. Heterocyclic Chem. 1971, 8, 495;
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16. a) Kohno, H.; Sekine, Y. Heterocycles 1996, 42, 141;
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18. 2). All new products gave correct analytical and spectroscopic data.
19. 4), concentrated and the remaining oil was flash- chromatographed [silica gel, hexane-EtOAc (65:35)] furnishing 1-carbethoxy-2-p-tosyl-6,7-dimethoxy-1,2,3,4- tetrahydroisoquinoline (76 mg, 0.182 mmol, 61%).
20. Menthyl ester 11 was obtained in 66% overall yield by esterification of 2-chloropropionic acid with (1R,2S,5R)-(-)-menthol in benzene under tosic acid catalysis, followed by LDA-mediated deprotonation of the resulting ester in THF at -78°C and reaction of the anionic species with PhSeBr. Analogously, 2 was prepared from commercially available ethyl 2-chloro propionate; see Ganem, B.; Ikota, N. J. Org. Chem. 1978, 43, 1607.
21. Kaufman, T. S. Synth. Commun. 1993, 23, 473, and references cited therein.
22. For chiral versions of the Pictet-Spengler reaction, see for instance a) Cox, E. D.; Hameker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44, and references cited therein; b) Dai, W. M.; Zhu, H. J.; Hao, X.-J. Tetrahedron:asymmetry 1996, 7, 1245; c) Soe, T.; Kawate, T.; Fukui, N.; Hino, T.; Nakagawa, M. Heterocycles 1996, 42, 347; d) Waldmann, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron 1994, 50, 1965.
23. For chiral versions of the Pictet-Spengler reaction, see for instance a) Cox, E. D.; Hameker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44, and references cited therein; b) Dai, W. M.; Zhu, H. J.; Hao, X.-J. Tetrahedron:asymmetry 1996, 7, 1245; c) Soe, T.; Kawate, T.; Fukui, N.; Hino, T.; Nakagawa, M. Heterocycles 1996, 42, 347; d) Waldmann, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron 1994, 50, 1965.
24. For chiral versions of the Pictet-Spengler reaction, see for instance a) Cox, E. D.; Hameker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44, and references cited therein; b) Dai, W. M.; Zhu, H. J.; Hao, X.-J. Tetrahedron:asymmetry 1996, 7, 1245; c) Soe, T.; Kawate, T.; Fukui, N.; Hino, T.; Nakagawa, M. Heterocycles 1996, 42, 347; d) Waldmann, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron 1994, 50, 1965.
25. For chiral versions of the Pictet-Spengler reaction, see for instance a) Cox, E. D.; Hameker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44, and references cited therein; b) Dai, W. M.; Zhu, H. J.; Hao, X.-J. Tetrahedron:asymmetry 1996, 7, 1245; c) Soe, T.; Kawate, T.; Fukui, N.; Hino, T.; Nakagawa, M. Heterocycles 1996, 42, 347; d) Waldmann, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron 1994, 50, 1965.
26. The Pictet-Spengler condensation of sulfonamide 10 with piperonal, giving a 3:4 diastereomeric mixture of products has been recently reported; see Nagarajan, K.; Chandrasekharan, J.; Rodrigues, P. J. J. Ind. Inst. Sci. 1994, 74, 247.