Direct, Regioselective N‑Alkylation of 1,3-Azoles

Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numer...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 1; pp. 16 - 19
Main Authors Chen, Shuai, Graceffa, Russell F, Boezio, Alessandro A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.01.2016
Amer Chemical Soc
Subjects
Alkylation
Azoles - chemistry
Catalysis
chemical structure
Chemistry
Chemistry, Organic
Magnesium - chemistry
Molecular Structure
nitrogen
organic compounds
Organometallic Compounds - chemistry
Physical Sciences
regioselectivity
Science & Technology
Stereoisomerism
NUCLEOSIDE
METHYLATION
PURINES
ANALOGS
BIOLOGICAL EVALUATION
INHIBITORS
IMIDAZOLES
DERIVATIVES
9-SUBSTITUTED TETRAHYDRODIAZEPINOPURINES
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.5b02994

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Summary:Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5b02994