期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 21, 页码 8243-8253出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo901759u
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资金
- Deutsche Forschungsgemeinschaft
The reaction of alpha,beta-unsaturated carbonyl compounds with aminoacetonitrile hydrochloride furnishes 3,5-disubstituted 3,4-dihydro-2H-pyrrole-2-carbonitriles in a one-pot reaction sequence. While these products can serve as starting materials for the preparation of polysubstituted pyrrolizidines, they are kinetically stable against the base-induced elimination of HCN. In contrast, their 2-substituted analogues obtained from alpha-substituted alpha-aminonitriles can be readily converted to the corresponding 2,3,5-trisubstituted pyrroles under microwave irradiation. The key step presumably involves the thermal electrocyclization of it stabilized 2-azapentadienyl anion Formed by condensation of the reactants and subsequent deprotonation.
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