One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines]

• Chao Wang,
• Yan-Hong Jiang and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2014, 10, 2671–2676, doi:10.3762/bjoc.10.281

• ; multicomponent reaction; one-pot reaction; spiro[indoline-3,4'-pyridine]; Introduction The spirooxindole system is the core structure of many natural products and pharmaceutically important structures with notable structural complexity and biological activities of great interest [1][2][3][4]. Accordingly, many

• reactions [19][20][21]. Recently, we and Perumal have demonstrated that the four-component reaction of arylamine, acetylenedicarboxylate, isatin and malononitrile can afford the spiro[indoline-3,4’-pyridine] derivatives in satisfactory yields [22][23][24]. We envisioned that functionalized spiro[indoline

• four-component reaction for the efficient synthesis of the functionalized spiro[indoline-3,4’-pyridine] derivatives [23] a mixture of benzohydrazide and dimethyl acetylenedicarboxylate in ethanol was firstly stirred at room temperature for about fifteen minutes. Then isatin and malononitrile as well as

Synthesis of functionalized spiro[indoline-3,4’-pyridines] and spiro[indoline-3,4’-pyridinones] via one-pot four-component reactions

• Li-Juan Zhang,
• Qun Wu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 846–851, doi:10.3762/bjoc.9.97

• malononitrile afforded the functionalized spiro[indoline-3,4’-pyridine] derivatives in good yields. Similar reactions with ethyl cyanoacetate successfully afforded the functionalized spiro[indoline-3,4’-pyridines] and spiro[indoline-3,4’-pyridinones] as the main products according to the structures of the

• Crystallographic Data Centre. General procedure for the synthesis of spiro[indoline-3,4’-pyridine] derivatives 1a–1p: In an analogous manner to our procedure published in [25], a solution of arylamine (2.0 mmol), methyl propiolate (2.0 mmol) in 5 mL ethanol was stirred at room temperature overnight. Then isatin

• domino reaction. Synthesis of spiro[indoline-3,4’-pyridine] 1a–1p by domino reaction. Synthesis of spiro[indoline-3,4’-pyridines] 2a–2h and spiro[indoline-3,4’-pyridinone] 3a–3n via domino reaction. Supporting Information Supporting Information File 8: Experimental details and detailed spectroscopic