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Volumn , Issue 23, 2008, Pages 4035-4040

Lewis acid catalyzed addition of pyrazoles to alkynes: Selective synthesis of double and single addition products

Author keywords

Addition reactions; Alkynes; Nitrogen heterocycles; Regioselectivity; Synthetic methods

Indexed keywords


EID: 53849133819     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800353     Document Type: Article
Times cited : (38)

References (80)
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    • Detailed information concerning isomer distributions in addition to spectral and analytical data of 1:1 adducts produced in the reactions of Table 2, Entries 1-6 and 12-14 are provided in the Supporting Information
    • Detailed information concerning isomer distributions in addition to spectral and analytical data of 1:1 adducts produced in the reactions of Table 2, Entries 1-6 and 12-14 are provided in the Supporting Information.
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    • 3 instead of AgOTf also proceeded in comparable yields (50% yield from 1m, 76% yield from 1n). However, an isomer of 4ma in the reaction of 1m was produced in a small amount (1% yield) together with 4ma. In the case of 1n, a mixture of four isomers including 4na and 5na was produced.
    • 3 instead of AgOTf also proceeded in comparable yields (50% yield from 1m, 76% yield from 1n). However, an isomer of 4ma in the reaction of 1m was produced in a small amount (1% yield) together with 4ma. In the case of 1n, a mixture of four isomers including 4na and 5na was produced.
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    • In ref.[13, N-methylpyrrole goes mainly to the Ph-attached carbon atom of 1n, contrary to the regioselectivity observed in Table 3, Entry 7
    • [13], N-methylpyrrole goes mainly to the Ph-attached carbon atom of 1n, contrary to the regioselectivity observed in Table 3, Entry 7.
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    • Proton signals that participate in hydrogen bonding such as C-H⋯X (X = heteroatom) are known to be shifted downfield in 1H NMR spectra. For example, see: H. Kawasaki, G. Sakane, T. Shibahara, Inorg. Chem. Commun. 2005, 8, 777-781.
    • Proton signals that participate in hydrogen bonding such as C-H⋯X (X = heteroatom) are known to be shifted downfield in 1H NMR spectra. For example, see: H. Kawasaki, G. Sakane, T. Shibahara, Inorg. Chem. Commun. 2005, 8, 777-781.


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