Electrosynthesis of dibenzonaphthyridine derivatives from 2,2-(2-nitrobenzyl)-2-substituted-acetonitriles

Author:

Jan Thierry,Dupas Béatrice,Floner Didier,Moinet Claude

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference7 articles.

1. Organic Electrochemistry;Lund,1991

2. The substrates 1a–f were prepared from 2-nitrobenzyl bromides and, respectively, malonitrile for 1a–d, benzyl cyanide for 1e and ethyl cyanoacetate for 1f. 1a–e were obtained by phase transfer catalysis using NBu4HSO4 in a mixture dichloromethane/2.5 M aqueous NaOH. 1f was prepared in ethanol containing solid sodium carbonate. 2-Nitrobenzyl bromides were obtained by refluxing overnight a mixture of 2-nitrotoluenes and N-bromosuccinimide in CCl4 in the presence of catalytic amount of benzoyl peroxide. The crude substrates 1a–f can be electrochemically reduced without further purification. Physical data for crystallized (dichloromethane/petroleum ether) 2,2-(2-nitrobenzyl)-malononitrile (1a): mp 168°C; 1H NMR δ (CDCl3) 4.15 (s, 4H), 7.75 (dd, 2H, J=8.2 Hz), 7.85–7.95 (m, 4H), 8.24 (dd, 2H, J=8.2 Hz); 13C NMR δ 39.5, 41.1, 115.6, 126.7, 128.9, 131.3, 134.8, 134.9, 150.2; IR (KBr) νCN=2245 cm−1, νNO2=1545 and 1344 cm−1. (1e) (Makosza, M.; Jagusztyn-Grochowska, J. M. Rocz. Chem. 1976, 50, 1859) and (1f) (Reissert, A. Chem. Ber. 1896, 29, 638) were previously described.

3. Über die Darstellung des Bis‐hydrocarbostyril‐3.3‐spirans und seine Nebenprodukte. (Über Spirane, IX)

4. Indirect electrolysis involving an ex-cell two-phase process. Reduction of nitrobenzenes with a titanium complex as mediator

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