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The chemistry of pyrazine and its derivatives. XI. The participation of tetramethylpyrazine in alkylation and aldol‐type reactions
Author(s) -
Chakrabartty Sujit K.,
Levine Robert
Publication year - 1966
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570030305
Subject(s) - chemistry , alkylation , phenyllithium , tetramethylpyrazine , pyrazine , aldol reaction , phenylmagnesium bromide , amide , organic chemistry , alkyl , halide , bifunctional , cyclobutane , medicinal chemistry , enamine , ring (chemistry) , catalysis , medicine , alternative medicine , pathology , reagent
Using sodium amide and phenyllithium as the condensing agents, tetramethylpyrazine has been alkylated with several alkyl halides to give mixtures of alkyltrimethylpyrazines and what are believed to be 2,5‐dialkyl‐3,6‐dimethylpyrazines. Evidence in support of the structures of the dialkylated compounds is presented for the case where the alkylating agent is n ‐butyl bromide. A number of carbinols have been prepared by the reaction of tetramethylpyrazine with aldehydes and ketones using phenyllithium as the condensing agent. One of these, 1‐(trimethylpyrazyl)‐2,4‐dimethyl‐2‐pentanol has been dehydrated to 1‐(trimethylpyrazyl)‐2, 4‐dimethyl‐1‐pentene.