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Molecules 1997, 2(4), 62-68; doi:10.3390/20400062
Article

o-Nitroaryl-bis(5-methylfur-2-yl)methanes as Versatile Synthons for the Synthesis of Nitrogen-Containing Heterocycles

1,*, 2, 1 and 2
Received: 25 October 1996 / Accepted: 17 January 1997 / Published: 10 April 1997
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Abstract

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.
Keywords: 2-Nitroaryldifurylmethanes; reduction; cycloaddition; N-containing heterocycles 2-Nitroaryldifurylmethanes; reduction; cycloaddition; N-containing heterocycles
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Butin, A.V.; Abaev, V.T.; Stroganova, T.A.; Gutnov, A.V. o-Nitroaryl-bis(5-methylfur-2-yl)methanes as Versatile Synthons for the Synthesis of Nitrogen-Containing Heterocycles. Molecules 1997, 2, 62-68.

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