Convenient novel syntheses of 1,1-bis(heteroaryl)alkanes

A variety of symmetrical 1,1-bis(heteroaryl)alkanes are prepared in excellent yields from the reaction of N-(alpha-benzotriazolylalkyl)carbamate 2 (itself easily available from the condensation of benzotriazole, an aldehyde, and an alkyl carbamate) with an excess of 2-methylthiophene or 2-methylfura...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 58; no. 16; pp. 4376 - 4381
Main Authors Katritzky, Alan R, Xie, Linghong, Fan, Wei Qiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.1993
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
N-<1-(BENZOTRIAZOL-1-YL)ALKYL>AMIDES
ROUTE
FURAN
ALKYLATION
CHEMISTRY
VERSATILE AMIDOALKYLATION REAGENTS
DERIVATIVES
N-SUBSTITUTED BENZOTRIAZOLES
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Summary:A variety of symmetrical 1,1-bis(heteroaryl)alkanes are prepared in excellent yields from the reaction of N-(alpha-benzotriazolylalkyl)carbamate 2 (itself easily available from the condensation of benzotriazole, an aldehyde, and an alkyl carbamate) with an excess of 2-methylthiophene or 2-methylfuran. When methyl N-(alpha-benzotriazolylalkyl)carbamate 2a is treated with 1 equiv of a heterocycle, the benzo-triazolylalkyl-substituted heterocycle is formed. These intermediates react further with other heterocycles to give unsymmetrical 1, 1-bis(heteroaryl)alkanes in good yields under mild conditions.
Bibliography:ark:/67375/TPS-3CT7X7XS-R
istex:9C3143FFBAB663346367C14D2339E6B08B85A414
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00068a036