Synthesis and stereochemistry of some heterocyclic saturated compounds based on l-p-nitrophenylserinol skeleton (III). 1,3-Dioxanic Schiff bases

Tetrahedron

Volumn 53, Issue 5, 1997, Pages 1909-1922

  Darabantu, Mircea ^a   Plé, Gerard ^b   Mager, Sorin ^a   Puscas, Camelia ^a   Cotora, Eleonora ^c  

^a BABE BOLYAI UNIVERSITY   (Romania)

^b UNIVERSITÉ DE ROUEN   (France)

^c NATIONAL INSTITUTE FOR CHEMICAL PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXANE DERIVATIVE; HETEROCYCLIC COMPOUND; SCHIFF BASE;

ARTICLE; CONFORMATION; DIASTEREOISOMER; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031550579     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01106-4     Document Type: Article

References (20)

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9. 9. Unpublished data. The enantiomerically pure (4S,5S)-aminodioxane 4b was also obtained following the same route as described for its racemic mixture (see ref. 8). The yield was unexpected by small (about 1-2%) due to its strong instability towards hydrolysis when the reaction mixture was processed. For continuous reproducible results, only racemic 4b was used.
10. 10. The results reported by Hauptmann, S.; Gabler, W., Z. Naturforsch. 1968, 23b, 111-112, could not be compared with ours. The structures reported as 1,3-dioxanic Schiff bases starting from TRIS (α, α, α-trimethylol-aminomethane) in reaction with (non)aromatic aldehydes are in complete contradiction with all TRIS literature data.
11. 11. Anteunis, M., J., O.; Tavernier, D.; Borremans, F., Heterocycles, 1976, 4, 293-371
12. 12. Smissman, E.; Schnettler, E., A.; Portoghese, J., J. Org. Chem., 1965, 30, (5), 797-805. See also comparable NMR data repored by: Ebens, R.; Kellog, M. R., Recl. Trav. Pays-Bas, 1990, 109, 552-560; Delmas, M.; Gaset, A., Informations Chimie 1982, 232, 151-158; Nordin, I., C.; Thomas, J., A.,Tetrahedron Lett. 1984, 25, (50), 5723-5724; El Gharbi, R.; Delmas, M.; Gaset, A., Tetrahedron, 1983, 39, (18), 2953-2963; Chenevert, R.; Voyer, N., Synth. Commun., 1985, 981-982; Delmas, M.; Gaset, A., Synth. Commun., 1980, 871-872; El Gharbi, R; Delmas, M.; Gaset, A.,Tetrahedron, 1986, 42, (4), 1192-1198
13. 12. Smissman, E.; Schnettler, E., A.; Portoghese, J., J. Org. Chem., 1965, 30, (5), 797-805. See also comparable NMR data repored by: Ebens, R.; Kellog, M. R., Recl. Trav. Pays-Bas, 1990, 109, 552-560; Delmas, M.; Gaset, A., Informations Chimie 1982, 232, 151-158; Nordin, I., C.; Thomas, J., A.,Tetrahedron Lett. 1984, 25, (50), 5723-5724; El Gharbi, R.; Delmas, M.; Gaset, A., Tetrahedron, 1983, 39, (18), 2953-2963; Chenevert, R.; Voyer, N., Synth. Commun., 1985, 981-982; Delmas, M.; Gaset, A., Synth. Commun., 1980, 871-872; El Gharbi, R; Delmas, M.; Gaset, A.,Tetrahedron, 1986, 42, (4), 1192-1198
14. 12. Smissman, E.; Schnettler, E., A.; Portoghese, J., J. Org. Chem., 1965, 30, (5), 797-805. See also comparable NMR data repored by: Ebens, R.; Kellog, M. R., Recl. Trav. Pays-Bas, 1990, 109, 552-560; Delmas, M.; Gaset, A., Informations Chimie 1982, 232, 151-158; Nordin, I., C.; Thomas, J., A.,Tetrahedron Lett. 1984, 25, (50), 5723-5724; El Gharbi, R.; Delmas, M.; Gaset, A., Tetrahedron, 1983, 39, (18), 2953-2963; Chenevert, R.; Voyer, N., Synth. Commun., 1985, 981-982; Delmas, M.; Gaset, A., Synth. Commun., 1980, 871-872; El Gharbi, R; Delmas, M.; Gaset, A.,Tetrahedron, 1986, 42, (4), 1192-1198
15. 12. Smissman, E.; Schnettler, E., A.; Portoghese, J., J. Org. Chem., 1965, 30, (5), 797-805. See also comparable NMR data repored by: Ebens, R.; Kellog, M. R., Recl. Trav. Pays-Bas, 1990, 109, 552-560; Delmas, M.; Gaset, A., Informations Chimie 1982, 232, 151-158; Nordin, I., C.; Thomas, J., A.,Tetrahedron Lett. 1984, 25, (50), 5723-5724; El Gharbi, R.; Delmas, M.; Gaset, A., Tetrahedron, 1983, 39, (18), 2953-2963; Chenevert, R.; Voyer, N., Synth. Commun., 1985, 981-982; Delmas, M.; Gaset, A., Synth. Commun., 1980, 871-872; El Gharbi, R; Delmas, M.; Gaset, A.,Tetrahedron, 1986, 42, (4), 1192-1198
16. 12. Smissman, E.; Schnettler, E., A.; Portoghese, J., J. Org. Chem., 1965, 30, (5), 797-805. See also comparable NMR data repored by: Ebens, R.; Kellog, M. R., Recl. Trav. Pays-Bas, 1990, 109, 552-560; Delmas, M.; Gaset, A., Informations Chimie 1982, 232, 151-158; Nordin, I., C.; Thomas, J., A.,Tetrahedron Lett. 1984, 25, (50), 5723-5724; El Gharbi, R.; Delmas, M.; Gaset, A., Tetrahedron, 1983, 39, (18), 2953-2963; Chenevert, R.; Voyer, N., Synth. Commun., 1985, 981-982; Delmas, M.; Gaset, A., Synth. Commun., 1980, 871-872; El Gharbi, R; Delmas, M.; Gaset, A.,Tetrahedron, 1986, 42, (4), 1192-1198
17. 12. Smissman, E.; Schnettler, E., A.; Portoghese, J., J. Org. Chem., 1965, 30, (5), 797-805. See also comparable NMR data repored by: Ebens, R.; Kellog, M. R., Recl. Trav. Pays-Bas, 1990, 109, 552-560; Delmas, M.; Gaset, A., Informations Chimie 1982, 232, 151-158; Nordin, I., C.; Thomas, J., A.,Tetrahedron Lett. 1984, 25, (50), 5723-5724; El Gharbi, R.; Delmas, M.; Gaset, A., Tetrahedron, 1983, 39, (18), 2953-2963; Chenevert, R.; Voyer, N., Synth. Commun., 1985, 981-982; Delmas, M.; Gaset, A., Synth. Commun., 1980, 871-872; El Gharbi, R; Delmas, M.; Gaset, A.,Tetrahedron, 1986, 42, (4), 1192-1198
18. 12. Smissman, E.; Schnettler, E., A.; Portoghese, J., J. Org. Chem., 1965, 30, (5), 797-805. See also comparable NMR data repored by: Ebens, R.; Kellog, M. R., Recl. Trav. Pays-Bas, 1990, 109, 552-560; Delmas, M.; Gaset, A., Informations Chimie 1982, 232, 151-158; Nordin, I., C.; Thomas, J., A.,Tetrahedron Lett. 1984, 25, (50), 5723-5724; El Gharbi, R.; Delmas, M.; Gaset, A., Tetrahedron, 1983, 39, (18), 2953-2963; Chenevert, R.; Voyer, N., Synth. Commun., 1985, 981-982; Delmas, M.; Gaset, A., Synth. Commun., 1980, 871-872; El Gharbi, R; Delmas, M.; Gaset, A.,Tetrahedron, 1986, 42, (4), 1192-1198
19. 12. Smissman, E.; Schnettler, E., A.; Portoghese, J., J. Org. Chem., 1965, 30, (5), 797-805. See also comparable NMR data repored by: Ebens, R.; Kellog, M. R., Recl. Trav. Pays-Bas, 1990, 109, 552-560; Delmas, M.; Gaset, A., Informations Chimie 1982, 232, 151-158; Nordin, I., C.; Thomas, J., A.,Tetrahedron Lett. 1984, 25, (50), 5723-5724; El Gharbi, R.; Delmas, M.; Gaset, A., Tetrahedron, 1983, 39, (18), 2953-2963; Chenevert, R.; Voyer, N., Synth. Commun., 1985, 981-982; Delmas, M.; Gaset, A., Synth. Commun., 1980, 871-872; El Gharbi, R; Delmas, M.; Gaset, A.,Tetrahedron, 1986, 42, (4), 1192-1198
20. 13. Proceeding paper. Part II.