Thioalkylation of Meldrum's acid with dialdehydes. Isopropylidene cis-2-hydroxy-6-phenylthiocyclohexane-1,1-dicarboxylate derivatives

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 8001-8004

  Eberle, Martin ^a   Ghorai, Alex ^a   Lawton, Richard G ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; GLUTARALDEHYDE; ISOPROPYLIDENE 2 HYDROXY 6 PHENYLTHIOCYCLOHEXANE 1,1 DICARBOXYLATE DERIVATIVE; THIOPHENOL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030813193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10174-5     Document Type: Article

References (29)

1. 5S : C 60.70, H 5.99, S 9.53, found C 60.79, H 6.04, S 9.48.
2. Using the above procedure: 6-p-tolythio derivative, mp 148-149°C; 6-acetylthio derivative, mp 122-124°C; 6-o-carboxyphenylthio derivative, mp 153°C; 6-2-hydroxyethylthio derivative, mp 130-131°C.
3. a) Baer, H.H. Adv. Carbohydr. Chem. Biochem. 1969, 24, 67;
4. b) Lichtenthaler, F.W. Angew. Chemie 1964, 76, 84.
5. c) Padeken, H.G.; von Schickh, O.; Segnitz, A. Houben-Weyl, Bd. X/1 1971, 259, 262.
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7. a) Lopez Aparicio, F.J.; Espinosa Ubeda, A.; Gallo Mezo, M.A. An. Quim. Ser. C 1976, 72, 981.
8. b) Lopez Aparicio, F.J.; Espinosa Ubeda, A.; Gallo Mezo, M.A. An. Quim. Ser. C 1979, 75, 916.
9. For a review of Meldrum's acid chemistry see McNab, H. Chem. Soc. Reviews 1978, 7, 345.
10. Even simple Knoevenagel condensation of n-butyraldehyde with Meldrum's acid affords a double adduct. Margaretha, P.; Polansky, O.E.; Tetrahedron Lett. 1969, 4983 reported the formation of a double adduct, mp 117-118°C. We believe the material isolated is in fact the dimer. See also Hedge, J.A.; Kunz C.W.; Snyder, H.R. J. Org. Chem. 1961, 26, 3166; Eistert, B.; Geiss, F. Ber. 1961, 94, 929.
11. Even simple Knoevenagel condensation of n-butyraldehyde with Meldrum's acid affords a double adduct. Margaretha, P.; Polansky, O.E.; Tetrahedron Lett. 1969, 4983 reported the formation of a double adduct, mp 117-118°C. We believe the material isolated is in fact the dimer. See also Hedge, J.A.; Kunz C.W.; Snyder, H.R. J. Org. Chem. 1961, 26, 3166; Eistert, B.; Geiss, F. Ber. 1961, 94, 929.
12. Even simple Knoevenagel condensation of n-butyraldehyde with Meldrum's acid affords a double adduct. Margaretha, P.; Polansky, O.E.; Tetrahedron Lett. 1969, 4983 reported the formation of a double adduct, mp 117-118°C. We believe the material isolated is in fact the dimer. See also Hedge, J.A.; Kunz C.W.; Snyder, H.R. J. Org. Chem. 1961, 26, 3166; Eistert, B.; Geiss, F. Ber. 1961, 94, 929.
13. Eberle M., Lawton R.G. Helv. Chim. Acta. 71:1988;1974.
14. 2O: C 50.86, H 4.85, N 13.48, S 6.17; found C 50.85, H 4.85, N 13.50, S 6.15.
15. Cf. procedure of Baer, H.H.; Fischer, H.O.L. J. Am. Chem. Soc. 1959, 81, 5184.
16. 7S: C 55.42, H 5.47, S 8.70; found C 55.33, H 5.56, S 8.69.
17. 7S: C 55.42, H 5.47, S 8.70; found C 55.52, H 5.55, S 8.73.
18. The oxidation was performed on the NMR-sample by adding an excess of mCPBA.
19. 6S: C 59.98, H 6.36, S 8.43, found C 59.97, H 6.32, S 8.32.
20. K. Fuji, S. Nakano, E. Fujita, Synthesis 1975, 276.
21. Hara, S.; Taguchi, H.; Yamamoto, H.; Nozaki, H. Tetrahedron Lett. 1975, 1545.
22. Brechühler H., Büchi H., Hatz E., Schreiber J., Eschenmoser A. Helv. Chim. Acta. 48:1965;1746.
23. 3): 7.54-7.51 (m, 2H); 7.30-7.23 (m, 3H); 7.06 (dd, J = 2.6, 4.8, 1H); 4.30-4.25 (br. apparent s, 1H); 3.77 (s, 3H); 2.38-1.97 (m, 4H); 1.76-1.66 (m, 2H).
24. 4S: C 59.98, H 5.75, S 11.44, found C 59.93, H 5.76, S 11.36.
25. a) Nelson, R.P.; McEuen, J.M.; Lawton, R.G. J. Org. Chem. 1969, 34, 1225.
26. b) Mitra, S.; Lawton, R. G. J. Am. Chem. Soc. 1979, 101, 3097.
27. c) Liberatore, F.A.; Comeau, R.D.; McKearin, J.M.; Pearson, D. A.; Belonga, B.Q.; Brocchini, S.J.; Kath, J.; Phillips, T.; Oswell, K.; Lawton, R.G. Bioconjugate Chem. 1990 1, 36.
28. d) Pan, V.; Hutchinson, D.K.; Nantz, M.H.; Fuchs, P.L. Tetrahedron 1989, 45, 467.
29. 2: C 68.35, H 6.78; found C 67.87, H 6.82.