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

doi:10.3390/20400062

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

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

Alexander V. Butin^1,*, Vladimir T. Abaev², Tat’yana A. Stroganova¹ and Andrey V. Gutnov²

¹ Research Laboratory of Furan Chemistry, Kuban State Technological University, Moskovskaya 2, Krasnodar, 350072, Russia ² 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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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

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MDPI and ACS Style

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.

AMA Style

Butin AV, Abaev VT, Stroganova TA, Gutnov AV. o-Nitroaryl-bis(5-methylfur-2-yl)methanes as Versatile Synthons for the Synthesis of Nitrogen-Containing Heterocycles. Molecules. 1997; 2(4):62-68.

Chicago/Turabian Style

Butin, Alexander V.; Abaev, Vladimir T.; Stroganova, Tat’yana A.; Gutnov, Andrey V. 1997. "o-Nitroaryl-bis(5-methylfur-2-yl)methanes as Versatile Synthons for the Synthesis of Nitrogen-Containing Heterocycles." Molecules 2, no. 4: 62-68.

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