Nucleophilic addition to electron-rich heteroaromatics: Dearomatizing anionic cyclizations of pyrrolecarboxamides
Nucleophilic addition to electron-rich heteroaromatics: Dearomatizing anionic cyclizations of pyrrolecarboxamides
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DOI：
10.1021/ol0364071
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发表时间：
2004-02-19
期刊：
影响因子：
5.2
通讯作者：
Pinto, I
中科院分区：
文献类型：
--
作者：
Clayden, J;Turnbull, R;Pinto, I
尽管吡咯环具有富电子的性质，但它容易受到有机锂的分子内亲核攻击。所得的脱芳构化阴离子环化产生新的5-或7-元杂环。通过N-苄基吡咯甲酰胺的环化形成新的5元环，伴随着原始吡咯的开环，得到3-氨基乙烯基吡咯啉酮。通过N-烯丙基吡咯甲酰胺的环化形成新的7元环，得到双环吡咯并氮杂卓酮。
Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.