Chemical and Electrochemical Reactions of Some Heterocyclic Compounds

Abstract

2.4.6-Trichlorophenylhydrazi ne reacted with acetvlcoumarin. camphor and acetaldehyde to give the corredsponding hydra ones which were transformed into a-chloroalkyl azo compounds when reacted with t-BuOCI. The obtained a-chloro azo compounds reacted with Lewis acids like SbCis or AICIJ to give unstable 1-aza-2-azoniaallene salts (Scheme I) which cannot be isolated in pure form.

Scheme 1

\ C=N-N-R'

t.-BuOCL CHClor Cl -IO"c t.o o•c. 3h 'c' = N- R'

HCL. lSbCL5 or ALCL l t. , -so•c \ + C=N=N-R'

R•' H'

?B-99% R11 'N

R'' ...a_,-

122 123 R', R'• H. Cl, olkyl. oryl. 1 , R'> l-but.yl. 4-chlorophenyl. 2.4,6-t.nchlorophenyl. elhowycorbonyl.

The salts 124 could be trapped by cycloaddition to unsaturated compounds as nitrites, acetylenes, isothiocyanates and carbodiimide providing new synthesais of new heterocyclic compounds.

The obtained heterocyclic derivatives 125, 127. 128, 129 and 130 and compounds 133-136 have been subjected to electrooxidation but unfonionately these derivatives show a great resistance towards the electrooxidation reaction.

Camphor reacted with ethylcarbazoate to give the corresponding hydrazone which reacted with t-BuOCI to give a-chloro azo compound which reacted with SbCis to give 1-aza-2-azoniaallene salt which react also with MeCN to give compond 13B. Nitrites underwent reaction with a-chloro azo compounds by (2+3) cycloaddition reaction to afford 1,2,4- triazolium salts (Scheme 2). The compound was studied by cyclic voltammetry and found that it resist oxidation and reduction.