Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer

A convenient synthesis of N-substituted heterocycles from primary and secondary alcohols and N-sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient intermediates miti...

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Bibliographic Details
Published inSynlett Vol. 26; no. 7; pp. 953 - 959
Main Authors Panteleev, Jane, Maguire, Robert J., Kung, Daniel W.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUBSTITUTION
ACTIVATION
SOLVENT-FREE CONDITIONS
MECHANISM
NATURAL-PRODUCTS
INDOLES
PYRAZOLE
S(N)2 reaction
CHEMISTRY
alkylation
N-ALKYLATION
sulfonyl transfer
pyrazoles
INHIBITORS
N-heterocycles
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Summary:A convenient synthesis of N-substituted heterocycles from primary and secondary alcohols and N-sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient intermediates mitigates challenges associated with isolation of these reactive species. N-Sulfonyl heteroarenes were found to be stable over prolonged time, and efficiently coupled to a variety of alcohols.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1379961