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Volumn 37, Issue 15, 1996, Pages 2577-2580

Reductive cyclization of N-iodoalkyl cyclic imides to nitrogen-fused polycyclic amides induced by samarium diiodide

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; ISOINDOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PYRROLE DERIVATIVE;

EID: 0029866808     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00374-7     Document Type: Article
Times cited : (41)

References (29)
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    • Chromatographic separation of 5d and 6d was not possible and the mixture was still obtained after dehydration with p-TsOH and 4 Å molecular sieves in dichloromethane. For isolation of 5d, known as pyrrolam C, from culture broth of Streptomyces olivaceus and structural determination, see: Grote, R.; Zeeck, A.; Stümpfel, J.; Zähner, H. Liebig's Ann. Chem. 1990, 525-530.
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    • note
    • 1H-COSY experiments. Also, the relative stabilities of 6e, 6g and their regioisomers were estimated using MOPAC PM3 semiempirical calculations. These results suggest that thermodynamics control dehydration regiochemistry. (matrix presented)
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    • Treatment of 4e or 4g with activated magnesium turnings in THF heated at reflux failed to give any cyclized product
    • Treatment of 4e or 4g with activated magnesium turnings in THF heated at reflux failed to give any cyclized product.
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    • note
    • +, 90), 136(33), 122(58), 108(47), 95(100), 80(22), 67(25), 55(75).
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