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Commercially available dimedone, benzaldehydes and ammonium acetate from Spectrochem were used. Progress of reactions was monitored by thin layer chromatography (TLC). NMR spectra were recorded in CDCl 3 at 300 MHz for 1 H and 75 MHz for 13 C on Bruker Avance DPX-300MHz. Chemical shifts were reported in δ (ppm) relative to CDCl 3 ( 13 C) as internal standards. Integrals are in accordance with assignments, coupling constants are given in Hz.The HRMS was recorded on a JOEL-AccuTOF JMS-T100LC Mass spectrometer having a DART source. The IR spectra were recorded on Spectrum RX-1 FTIR, Perkin Elmer. Yields refer to quantities obtained after chromatography. Melting point of compounds were recorded on LABINDIA make melting point apparatus and are uncorrected. General experimental procedure Synthesis of 3-amino-5,5-dimethylcyclohex-2-enone (2):A mixture of dimedone (1) (1.0 g, 7.1 mmol) and NH 4 OAc (1.32 g, 21.4 mmol) was heated in 30 mL of water at 80 ᴏ C for 5 hours. After the TLC indicated the consumption of dimedone (2), the reaction mixture was extracted with ethyl acetate several times. The combined organic layer was dried over sodium sulphate and evaporated to provide enaminone (2) (0.9 g, 90%) as light yellow solid.

The synthetic utility of C1 and C3 nucleophilic behavior of acetylacetone in a reaction with isatin for two distinct pharmaceutically relevant scaffolds 3‐substituted 3‐hydroxyoxindole and spirooxindole‐pyran in water is presented. The protocol offers environmentally benign conditions, wide substrate scope, and good to the very good chemical yield of products. The developed methodology has the potential to generate a library of useful synthetic compounds that are of pharmaceutical interest. A plausible mechanism for the formation of products based on the outcome of the reaction is also rationalized.

Commercially available isatin, Dimedone and Ammonium acetate from Aldrich, Spectrochem, Himedia were used. The progress of reactions was monitored by thin layer chromatography (TLC). 1D and 2D NMR spectra were recorded in MeOH-d 4 /DMSO-d 6 at 300/400 MHz for 1 H and 75/100 MHz for 13 C on Bruker Avance DPX-300MHz/DPX-400MHz. Chemical shifts were reported in δ (ppm) relative to DMSO-d 6 as internal standards. Integrals are in accordance with assignments, coupling constants are given in Hz.The HRMS was recorded on a JOEL-AccuTOF JMS-T100LC Mass spectrometer having a DART source. Yields refer to quantities obtained after column chromatography.  Characterization data for compounds 3-(2-amino-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3-hydroxyindolin-2-one (3a): Isolated as