Solid phase-mediated synthesis of isonitriles

Tetrahedron Letters

Volumn 43, Issue 40, 2002, Pages 7201-7203

  Launay, Delphine ^a   Booth, Susan ^b   Clemens, Ian ^c   Merritt, Andrew ^d   Bradley, Mark ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

^c ELI LILLY AND COMPANY   (United States)

^d GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; ISONITRILE DERIVATIVE;

ARTICLE; MICROWAVE IRRADIATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID; SYNTHESIS;

EID: 0037201161     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01672-6     Document Type: Article

References (13)

1. Passerini M. Gazz. Chim. Ital. 51:1921;126.
2. Ugi I., Betz W., Fetzer U., Offermann K. Chem. Ber. 94:1961;2814-2816.
3. Dömling A., Ugi I. Angew. Chem., Int. Ed. 39:2000;3168-3210.
4. Bauer S.M., Armstrong R.W. J. Am. Chem. Soc. 121:1999;6355-6366.
5. Weber L., Illgen K., Almstetter M. Synlett. 3:1999;366-374.
6. Dömling A., Ugi I. Angew. Chem., Int. Ed. 32:1993;563-564.
7. Dömling A. Curr. Opin. Chem. Biol. 4:2000;318-323.
8. For methods of isonitrile synthesis, see: (a) Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766-3769; (b) Obrecht, R.; Herrmann, R.; Ugi, I. Synthesis 1985, 400-402; (c) Kercher, T.; Livinghouse, T. J. Org. Chem. 1997, 62, 805-812.
9. For methods of isonitrile synthesis, see: (a) Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766-3769; (b) Obrecht, R.; Herrmann, R.; Ugi, I. Synthesis 1985, 400-402; (c) Kercher, T.; Livinghouse, T. J. Org. Chem. 1997, 62, 805-812.
10. For methods of isonitrile synthesis, see: (a) Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766-3769; (b) Obrecht, R.; Herrmann, R.; Ugi, I. Synthesis 1985, 400-402; (c) Kercher, T.; Livinghouse, T. J. Org. Chem. 1997, 62, 805-812.
11. Ho T.-L., Jana G.H. J. Org. Chem. 64:1999;8965-8967.
12. From Novabiochem. Sulfonyl chloride polystyrene resin 100-200 mesh. The polymer matrix is copoly(styrene-1% DVB). Substitution: 2.9 mmol/g.
13. 4 and concentrated to afford 40 mg of the expected compound, in 70% yield and 98% purity.