%0 Journal Article
%T o-Nitroaryl-bis(5-methylfur-2-yl)methanes as Versatile Synthons for the Synthesis of Nitrogen-Containing Heterocycles
%A Alexander V. Butin
%A Vladimir T. Abaev
%A TatĄŻyana A. Stroganova
%A Andrey V. Gutnov
%J Molecules
%D 1997
%I MDPI AG
%R 10.3390/20400062
%X 2-Nitroaryldifurylmethanes 1a and 1b, readily available by condensation of 2-nitrobenzaldehyde and 6-nitroveratraldehyde with 2-methylfuran, were transformed into indole, cinnoline and benzothiazine-3,1 derivatives. The reduction of 2-nitroaryldifurylmethanes gave the corresponding anilines 2a,b or indole 3 depending on the reaction conditions. A plausible mechanism for the last reaction involving intramolecular heterocyclic addition between a nitroso-group and a furan ring is proposed. Diazotisation of the amine 2b gave a cinnoline derivative - a product of intramolecular oxidative furan ring opening. Treatment of isothiocyanates 7a,b with perchloric acid resulted in a new rearrangement with furan ring migration leading to the 4-Hbenzothiazine-3,1 derivatives.
%K 2-Nitroaryldifurylmethanes
%K reduction
%K cycloaddition
%K N-containing heterocycles
%U http://www.mdpi.com/1420-3049/2/4/62