Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 15, Issue -, Pages 2623-2630Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.15.255
Keywords
[3+2] cycloaddition; isoxazole; pyrrole; silver catalysis; ynamide
Categories
Funding
- NSFC [21402106]
- Shandong Natural Science Foundation [ZR2018JL013, ZR2018MB014]
- Qufu Normal University for Research Start-up Foundation [bsqd20130115]
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A formal [3 + 2] cycloaddition between ynamides and unprotected isoxazol-5-amines has been developed in the presence of catalytic AgNTf2 in an open flask. By the protocol, a variety of functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives can be obtained in up to 99% yield. The reaction mechanism might involve the generation of an unusual alpha-imino silver carbene intermediate (or a silver-stabilized carbocation) and subsequent cyclization/isomerization to build the significant pyrrole-3-carboxamide motif. The reaction features the use of an inexpensive catalyst, simple reaction conditions, simple work-up without column chromatographic purification for most of products and high yields.
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