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Synthesis of N ‐Fused “Lactendiynes”
Author(s) -
Banfi Luca,
Guanti Giuseppe
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199808)1998:8<1543::aid-ejoc1543>3.0.co;2-z
Subject(s) - enediyne , chemistry , reactivity (psychology) , lactam , stereochemistry , hydrolysis , combinatorial chemistry , fusion , organic chemistry , medicine , linguistics , philosophy , alternative medicine , pathology
New “lactendiynes”, characterized by the fusion at C‐4 and N‐1 of a β‐lactam with a hydroxylated 10‐membered cyclic enediyne, were synthesized. Studies on their reactivity have shown that this type of fusion with the azetidinone represents a sufficient “safety‐catch” against cycloaromatization. These compounds are relatively reactive toward basic hydrolysis, affording monocyclic enediynes which undergo fast cycloaromatization at room temperature.