A Method for Pyrrole Synthesis through Intramolecular Cyclization of gamma-Alkynyl Oximes Promoted by Sml(2)

A new strategy for the synthesis of pyrrole through intramolecular cyclization of gamma-alkynyl oximes promoted by Smt(2) is reported for the first time. In contrast to the prior methods, the selection of oxime instead of oxime ether or ester as substrate makes the synthetic method without accompani...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 54; no. 24; pp. 5491 - 5499
Main Authors Wang, Yiqiong, Zhang, Lingyu, Zhang, Songlin
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 15.12.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ROUTE
TOYOCAMYCIN
DESIGN
ANALOGS
atomic economic
CATALYST
oxime
pyrrole
gamma-alkynyl
Sml
N-centered radical
ESTERS
FUNCTIONAL-GROUPS
DERIVATIVES
EFFICIENT
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Summary:A new strategy for the synthesis of pyrrole through intramolecular cyclization of gamma-alkynyl oximes promoted by Smt(2) is reported for the first time. In contrast to the prior methods, the selection of oxime instead of oxime ether or ester as substrate makes the synthetic method without accompaniment of organic waste (ArCO2H, AcOH, or ROH) because the hydroxyl group in oxime acts as the leaving group and is finally removed in the form of water molecule in the reaction. From a synthetic point of view, a series of pyrroles were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1932-5749