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

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

Research Laboratory of Furan Chemistry, Kuban State Technological University, Moskovskaya 2, Krasnodar, 350072, Russia
Department of Organic Chemistry, North Ossetian State University,Vatutina 46, Vladikavkaz, 362025, Russia
Author to whom correspondence should be addressed.
Received: 25 October 1996 / Accepted: 17 January 1997 / Published: 10 April 1997
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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. View Full-Text
Keywords: 2-Nitroaryldifurylmethanes; reduction; cycloaddition; N-containing heterocycles 2-Nitroaryldifurylmethanes; reduction; cycloaddition; N-containing heterocycles

Scheme 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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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