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Volumn , Issue 11, 2003, Pages 1688-1692

Microwave-assisted soluble polymer-supported synthesis of benzopiperazinones

Author keywords

Combinatorial synthesis; Microwave assisted; Quinoxaline 2 ones

Indexed keywords

FLUORIDE; NITRO DERIVATIVE; PIPERAZINE DERIVATIVE; POLYMER; QUINOXALINE DERIVATIVE;

EID: 0042912871     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41427     Document Type: Article
Times cited : (36)

References (35)
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    • For microwave-assisted solid-phase combinatorial synthesis, see: (a) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, R. A. J. Comb. Chem. 2002, 4, 95. (c) Martin, B.; Sekljic, H.; Chassaing, C. Org. Lett. 2003, 5, 1851.
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    • For microwave-assisted solid-phase combinatorial synthesis, see: (a) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, R. A. J. Comb. Chem. 2002, 4, 95. (c) Martin, B.; Sekljic, H.; Chassaing, C. Org. Lett. 2003, 5, 1851.
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    • note
    • Discover focused microwave oven from CEM was used for our study.
  • 34
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    • note
    • (b) Jacobsen et al. reported the solution phase synthesis of 1,2,3,4-tetrahydroquinoxalin-2-ones using similar cyclization. They observed primary amino group stands to be more nucleophilic than adjacent substituted NH group. Probably steric hindrance of t-butyl group is the key factor to facilitate the acid chloride to opt primary amine in their work (Scheme 3).
  • 35
    • 0042160831 scopus 로고    scopus 로고
    • note
    • 2O and dried in vacuum. Polymer support of 8m was cleaved by exposing it to microwave (150 W) for 10 min in sodium methoxide solution. Progress of cleavage was monitored on TLC [solvent: EtOAc-n-hexane (1:2)]. Separation of 2-arm PEG from the desired products was achieved by precipitation in ethanol to give crude mixtures of compounds 9m and 10m in 90% combined yield and 93% (53% and 40%) HPLC purity (UV detection at λ = 254 nm. Column: Sphereclone 5u Si (250 x 4.6 nm); gradient: 50% EtOAc/n-hexane; flow rate: 1 mL/min).


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