INDOLE DERIVATIVES: 128. SYNTHESIS AND PROPERTIES OF 5,6- AND 4,5-ETHYLENEDIOXYINDOLES

Article abstract of DOI:10.1007/BF00474350

Reaction of 3,4-ethylenedioxyphenyldiazonium chloride with ethyl 2-methylacetoacetate and subsequent cyclization of the 3,4-ethylenedioxyphenylhydrazone of ethyl pyruvate gives a 1:4 mixture of 4,5- and 5,6-ethylenedioxy-2-etoxycarbonylindoles, respectively, from which 4,5- and 5,6-ethylenedioxyindoles are formed by subsequent hydrolysis and decarboxylation.Mannich and Vilsmeyer reactions as well as acetylation and azo coupling have been studied for 5,6-ethylenedioxyindole.