21418-71-3Relevant articles and documents
Oxidation strategy for the synthesis of regioisomeric spiroisobenzofuranopyrroles: Facile entries to spiro[isobenzofuran-1,2′-pyrrole] and Spiro[isobenzofuran-1,3′-pyrrole] derivatives
Fan, Yefeng,Liu, Song,Chen, Nanyang,Shao, Xusheng,Xu, Xiaoyong,Li, Zhong
supporting information, p. 393 - 403 (2015/02/19)
Two practical and efficient approaches have been developed to synthesize two kinds of racemic spiroisobenzofuranopyrrole analogues as regioisomers. In the presence of sodium periodate, cis-indeno[1,2-b]pyrrol-4(1H)-ones were converted into spiro[isobenzofuran-1,2′-pyrrole] derivatives by a two-step process. In addition, oxidative reactions promoted by lead tetraacetate were demonstrated using cis-indeno[2,1-b]pyrrol-8(1H)-ones as substrates, affording spiro[isobenzofuran-1,3′-pyrrole] derivatives. The remarkable features of two approaches included mild and convenient reaction conditions, a broad substrate scope, and moderate to excellent yields. Possible mechanisms were proposed based on the comparison of the intermediates and products.
The aza-ene or the Michael addition? Examination of an unusual substituent effect on the reaction of heterocyclic ketene aminals with ethyl propiolate
Zhao, Mei-Xin,Wang, Mei-Xiang,Huang, Zhi-Tang
, p. 1309 - 1316 (2007/10/03)
Heterocyclic ketene aminals having at least one secondary amino group underwent the aza-ene reaction with ethyl propiolate under various conditions to yield the corresponding adducts, which were readily transformed into the δ-lactam fused heterocyclic products with or without the aid of sodium ethoxide in refluxing ethanol, while the ester- and cyano-substituted tertiary enediamines acted as the strong Michael donor to add to ethyl propiolate in a polar or a protic solvent. The unusual substituent effect on the reactivity and mechanism was discussed.
