Synthesis of polymeric supports with spacer-modified triazene linkers: Aldol and Grignard reactions of immobilized nortropinone

Tetrahedron Letters

Volumn 44, Issue 12, 2003, Pages 2441-2444

  Lazny, Ryszard ^a   Nodzewska, Aneta ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

Amines; Polymer support; Solid phase synthesis; Triazenes

Indexed keywords

KETONE DERIVATIVE; NORTROPINONE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; DRUG SYNTHESIS; GRIGNARD REACTION; IMMOBILIZATION; PRECURSOR; SOLID;

EID: 0037450971     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00345-9     Document Type: Article

References (16)

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5. (b) Bräse, S.; Dahmen, S. In Handbook of Combinatorial Chemistry; Nicolaou, K. C.; Hanko, R.; Hartwig, W., Eds.; Wiley: New York, 2002; Chapter 4.
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8. Lazny, R.; Sienkiewicz, M., unpublished results.
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12. (a) Bräse S., Dahmen S., Pfefferkorn M. J. Comb. Chem. 2:2000;710-715; (b) For the preparation of resin 12 hydrochloride through reduction, see: Ref. 5; (c) Gordon K.H., Balasubramanian S. Org. Lett. 3:2001;53-56.
13. (a) Bräse S., Dahmen S., Pfefferkorn M. J. Comb. Chem. 2:2000;710-715; (b) For the preparation of resin 12 hydrochloride through reduction, see: Ref. 5; (c) Gordon K.H., Balasubramanian S. Org. Lett. 3:2001;53-56.
14. 3): δ 156.9, 143.6, 121.3, 114.8, 66.9, 65.3, 46.0, 29.8, 13.0. The resin 12a (0.300 g) was swollen in DCM, cooled to 0°C and washed with a chilled 10% TFA in DCM (3 mL, 10 min), DCM, 10% TFA in DCM (3 mL, 10 min) and DCM (5×4 mL). Then the cold (-18°C) solution of 9 (10 equiv.) in DCM was added and the suspension was shaken and slowly warmed up to rt. After washing, the resulting gel was treated with 10% TFA in DCM and the cleaved amine was converted to the hydrochloride and dried to give pure 9·HCl (0.034 g, 0.84 mmol/g).
15. 2NH·HCl or 9·HCl) was used for comparing results.
16. 13C NMR, IR and CHN analyses.