Nucleophilic substitution reaction of 4-bromobenzo [1,2-c;3,4-c′] bis [1,2,5] thiadiazole and reduction of hydroxy and methoxy derivative to the corresponding 1,2,3,4-benzenetetraamine

doi:10.3987/COM-91-S84

Paper

Nucleophilic substitution reaction of 4-bromobenzo [1,2-c;3,4-c′] bis [1,2,5] thiadiazole and reduction of hydroxy and methoxy derivative to the corresponding 1,2,3,4-benzenetetraamine

Published Apr 1, 1992 · S. Mataka*, Youji Ikezaki, Kazufumi Takahashi

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Q4 SJR score

10

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0

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Abstract

Bromobenzo[1,2-c;3,4-c']bis[1,2,5]thiadiazole (2a) reacted with a series of nucleophiles to give alkoxy-, propylthio-, and amino-substituted derivatives (3, 8, and 9). Reaction of 2a with allyl alcohol at room temperature gave allyl ether (3e) which, on being heated, rearranged to 4-allyl-5-hydroxy derivative (4). Treatment of methoxy and ethoxy derivatives (3a and 3b) with hydrobromic acid gave hydroxy compound (5). Reduction of 3a and 5 gave the corresponding 1,2,3,4-benzenetetraamine (10.3HCl) and (11.2HCl), respectively. Reduction of piperidino derivative (9b) gave a mixture of hydrochlorides of 1,2,3,4-benzenetetraamine (1a), 11, and 5-piperidino-1,2,3,4-benzenetetraamine (12)

Study Snapshot

This study demonstrates the potential of bromobenzo[1,2-c;3,4-c′]bis[1,2,5]thiadiazole for the synthesis of 1,2,3,4-benzenetetraamine, a key intermediate in the synthesis of cyclohexanedioic

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Nucleophilic substitution reaction of 4-bromobenzo [1,2-c;3,4-c′] bis [1,2,5] thiadiazole and reduction of hydroxy and methoxy derivative to the corresponding 1,2,3,4-benzenetetraamine

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