Solid-phase synthesis of dibenzoxazepinones

Tetrahedron Letters

Volumn 44, Issue 44, 2003, Pages 8169-8172

  Hone, Neal D ^a   Salter, James I ^a   Reader, John C ^a  

^a Millennium Pharmaceuticals Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; KETONE DERIVATIVE; PHENOL DERIVATIVE; RESIN;

AMINATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; TECHNIQUE;

EID: 0141656513     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.037     Document Type: Article

References (17)

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9. (c) (Novabiochem (3-formylindolyl)acetamidomethyl 1% DVB polystyrene, 1 mmol/g.
10. +).
11. Doyle M.P., Siegfried B., Dellaria J.F. Jr. J. Org. Chem. 42:1977;2426-2430.
12. Kornblum N., Iffland D.C. J. Am. Chem. Soc. 71:1949;2137-2143.
13. Novabiochem 1% DVB polystyrene, 1.3 mmol/g.
14. Alkyl halides used were methyl iodide, iodoacetonitrile, allyl bromide, bromoacetamide, methyl bromoacetate, 2-chlorobenzyl bromide, 3-chlorobenzyl bromide, 4-chlorobenzyl bromide, 2-methoxybenzyl bromide, 3-methoxybenzyl bromide, 4-methoxybenzyl bromide, 2-methylbenzyl bromide, 3-methylbenzylbromide, 4-methylbenzyl bromide, 2-fluorobenzyl bromide, 3-fluorobenzyl bromide, 4-fluorobenzyl bromide, 2-cyanobenzyl bromide, 3-cyanobenzyl bromide, 4-cyanobenzyl bromide, benzyl bromide, 2,3-difluorobenzyl bromide and 2,4-difluorobenzyl bromide. The free NH resin ( 20 ) was also used in step xii.
15. Amines used were ammonia, methylamine, ethanolamine, 1-amino-2-propanol, N-methylethylenediamine, N,N-dimethylethylenediamine, 2-methoxyethylamine, cyclopropylamine, 3-amino-1,2-propanediol, morpholine, N-methylpiperazine, tetrahydrofurfurylamine, n-propylamine, pyrrolidine, 2,2,2-trifluoroethylamine and 3-pyrrolidinol.
16. +).
17. Novabiochem MP-polystyrene anhydride resin, 6 mmol/g.