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1 article(s) from Bakhonsky, Vladyslav

Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts

Grzegorz Mlostoń,
Małgorzata Celeda,
Katarzyna Urbaniak,
Marcin Jasiński,
Vladyslav Bakhonsky,
Peter R. Schreiner and
Heinz Heimgartner

Beilstein J. Org. Chem. 2019, 15, 497–505, doi:10.3762/bjoc.15.43

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Scheme 1: Synthesis of 2-unsubstituted imidazole N-oxides 1 from α-hydroxyiminoketones 2 and formaldimines 3.

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Scheme 2: Preparation of adamantyloxyamine (4) and its conversion into N-(adamantyloxy)formaldimine (6a); Ad ...

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Scheme 3: Synthesis of 1-(adamantyloxy)imidazole 3-oxides 7a–e and 1-adamantylimidazole 3-oxides 7f,g in acet...

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Scheme 4: Deoxygenation of 1-(adamantyloxy)imidazole 3-oxides 7a–d and isomerization of 7b into imidazole-2-o...

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Scheme 5: Conversions of imidazole 3-oxides 7a–d into 1-(adamantyloxy)imidazole-2-thiones 10a–d via sulfur tr...

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Scheme 6: Syntheses of the non-symmetric 1,3-dialkoxyimidazolium bromides 13a–c and 1-alkyl-3-alkoxyimidazoli...

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Scheme 7: Attempted O-adamantylation of imidazole N-oxide 7a with adamantan-1-yl trifluoroacetate and subsequ...

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Scheme 8: Synthesis of the symmetric 1,3-di(adamantyloxy)imidazolium bromide (15) and its transformation to 1...

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Published 19 Feb 2019

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