Synthesis of Nitroalkenes Involving a Cooperative Catalytic Action of Iron(III) and Piperidine: A One‐Pot Synthetic Strategy to 3‐Alkylindoles, 2H‐Chromenes and N‐Arylpyrrole

Abstract

An efficient and simple strategy has been developed to synthesize various substituted nitroalkenes involving a cooperative catalytic system of FeCl3 and piperidine. This dual catalytic protocol simultaneously activates both electrophile and nucleophile and works under mild reaction conditions so that many sensitive functional groups were tolerated. Moreover, this cooperative catalytic reaction is also suitable for various one‐pot reactions involving nitroalkenes such as, 2H‐chromenes, N‐arylpyrrole and Michael reaction with indole. Notably, this method is low‐cost, efficient and environmentally friendly.

An Efficient Synthesis of 1,2,4-Trisubstituted Imidazoles from Arylacetic Acids andN-Arylbenzamidines via Simultaneous C-H and N-H Bond Activation

“…α‐hydroxy carboxylic acid on dehydrogenation followed by decarboxylation offered aromatic aldehyde A . On the other hand, N−H activation, of N ‐arylbenzamidine led to its condensation with aromatic aldehyde A to form 2,4‐di‐azadiene which upon Michael addition, with CH 3 NO 2 produced ring annulated intermediate B . The 5‐exo‐trig cyclization of intermediate B resulted in formation of imidazole backbone which eventually on β‐hydride elimination offers desired 1,2,4‐trisubstituted imidazole 3 .…”

The synthesis of N‐benzoylindoles as inhibitors of rat erythrocyte glucose‐6‐phosphate dehydrogenase and 6‐phosphogluconate dehydrogenase

“…[29] A mixture of aldehyde (1 mmol), nitro alkane (6 mmol), and piperidine (0.1 mmol) were added sequentially to oven-dried flask containing toluene as solvent (10 mL), then anhydrous FeCl 3 (0.1 mmol) was added into the reaction medium. [29] A mixture of aldehyde (1 mmol), nitro alkane (6 mmol), and piperidine (0.1 mmol) were added sequentially to oven-dried flask containing toluene as solvent (10 mL), then anhydrous FeCl 3 (0.1 mmol) was added into the reaction medium.…”

Highly Efficient Tetranuclear ZnII2LnIII2 Catalysts for the Friedel–Crafts Alkylation of Indoles and Nitrostyrenes

“…For the reaction between indole and β-nitrostyrene, various catalytic systems have been proposed. These include hydrogen-bond-based compounds [11][12][13][14][15][16] such as thiourea [11,14,15,[17][18][19][20], phosphoric acid [16], silanediols [21,22], sulfamic acid [23] and 2,6-bis(amido)benzoic acid [24]; metal based compounds [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41] such as Al III [25,39], Cu II [26][27][28][29][30]41], Zn II [31][32][33][34][35]40,…”