Chlorosulfonyl Isocyanate Reactions with N-(Alkoxycarbonyl)-2-azabicyclo[2.2.0]hex- 5-enes. Regiospecific Two-Atom Insertion Pathways

Chlorosulfonyl Isocyanate Reactions with N-(Alkoxycarbonyl)-2-azabicyclo[2.2.0]hex- 5-enes. Regiospecific Two-Atom Insertion Pathways

Addition of the uniparticulate electrophile chlorosulfonyl isocyanate to the nitrogen atom of N-(alkoxycarbonyl)-2-azabicyclo[2.2.0]hex-5-enes 1 is followed by ring cleavage and recombination. The parent 4-methyl, 5-methyl, 5-bromo, and 5-phenyl azabicycles 1a−f afforded novel 2,4-diaza-3-oxo-bicycl...

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Veröffentlicht in:Journal of organic chemistry 2003-02, Vol.68 (4), p.1626-1629
Hauptverfasser: Krow, Grant R, Lester, Walden S, Lin, Guoliang, Fang, Yuhong, Carroll, Patrick J
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Beschreibung
Zusammenfassung:Addition of the uniparticulate electrophile chlorosulfonyl isocyanate to the nitrogen atom of N-(alkoxycarbonyl)-2-azabicyclo[2.2.0]hex-5-enes 1 is followed by ring cleavage and recombination. The parent 4-methyl, 5-methyl, 5-bromo, and 5-phenyl azabicycles 1a−f afforded novel 2,4-diaza-3-oxo-bicyclo[4.2.0]oct-7-enes 10a−f. The 3-endo-phenyl azabicycle 1g rearranged to a 6-styryl-1,3-diaza-2-oxo-cyclohex-4-ene 12.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020655d