ALDOL CONDENSATION OF N-ALKYLATED-3-ARYL-4,6-DIMETHOXY-7-FORMYLINDOLES AS A GOOD METHOD FOR THE SYNTHESIS OF 1-ARYL-6,8-DIMETHOXYPYRROLO[3,2,1-hi]INDOLE-4-CARBOXYLATES | Zendy

Jumina Jumina | Zendy

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ALDOL CONDENSATION OF N-ALKYLATED-3-ARYL-4,6-DIMETHOXY-7-FORMYLINDOLES AS A GOOD METHOD FOR THE SYNTHESIS OF 1-ARYL-6,8-DIMETHOXYPYRROLO[3,2,1-<i>hi</i>]INDOLE-4-CARBOXYLATES

Author(s) -

Jumina Jumina

Publication year - 2010

Publication title -

indonesian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.273

H-Index - 14

eISSN - 2460-1578

pISSN - 1411-9420

DOI - 10.22146/ijc.21735

Subject(s) - chemistry , formylation , alkylation , aldol condensation , sodium hydride , aryl , yield (engineering) , reagent , intramolecular force , condensation , indole test , tetrahydrofuran , medicinal chemistry , aldol reaction , organic chemistry , catalysis , solvent , alkyl , materials science , physics , metallurgy , thermodynamics

Alkylation of 3-aryl-4,6-dimethoxyindole 3a and 3b with methyl and ethyl -bromoacetates afforded good yields of indol-1-ylacetates 4. Treatment of these indoles 4 with the Vilsmeier formylation reagent gave formylindoles 5 in 54-81 % yield. These formylindole 5 underwent intramolecular aldol condensation when treated with sodium hydride in tetrahydrofuran to give pyrroloindole-4-carboxylates 6 in 30-60 % yield. Structural assignment based on spectroscopic data confirmed the structure of the synthesized pyrroloindoles. In the case of pyrroloindole 6c, the structure of this molecule was also proven by X-ray crystallography data.

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