Solid phase synthesis of tricyclic nitrogen heterocycles via intramolecular Diels-Alder reaction of furans

Synlett

Volumn , Issue 10, 1999, Pages 1609-1611

  Paulvannan, K ^a   Chen, Tao ^a   Jacobs, Jeffrey W ^a,b  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

^b Versicor Inc   (United States)

Author keywords

Furan; Intramolecular Diels Alder reaction; Maleic anhydride; Solid phase synthesis; Tricyclic nitrogen heterocycles

Indexed keywords

FUMARIC ACID; FURAN DERIVATIVE; MALEIC ACID; NITROGEN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; MOLECULAR INTERACTION; SOLID; SYNTHESIS;

EID: 0032825896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2909     Document Type: Article

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26. Among all the resins examined, ArgoGel Rink amide resin (loading 0.33 mmol/g) gave the best results.
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28. Treatment of secondary amines such as morpholine and piperidine with 7a resulted in the isolation of a mixture of products. The desired products were isolated in low yields (30 to 50%) after chromatographic purification. No further optimization study was pursued and our study was limited to primary amines only.