PDF《5,10(4H,11H)-dione derivatives》

S1 Supporting information L-proline catalyzed multicomponent reactions: Facile access to 2H-benzo[g]pyrazolo[3,4-b]quinoline- 5,10(4H,11H)-dione derivatives Shaik Karamthulla,a Suman Pal,a Tasneem Parvin,b and Lokman H.

Choudhury*a aDepartment of Chemistry, Indian Institute of Technology Patna, Patna-800013, India. bDepartment of Chemistry, National Institute of Technology Patna, Ashok Rajpath, Patna -800005, India. Email: [email protected] Table of contents 1. General information.S2 2. General procedure of synthesis S2 3. Copies of 1H and 13C NMR spectra of compounds.S3-S18 S2 1. General information. All reagents and chemicals required for the reactions were procured from commercial sources and used without further purification. IR spectra were recorded in Shimadzu FTIR spectrophotometer. 1H NMR spectra and 13C NMR spectra were recorded on 500, 400,

300 MHz spectrometer in DMSO-d6 using TMS as internal reference. Elemental analyses were carried out in a Perkin Elmer

2400 automatic CHN analyzer or Elementer Vario EL III. All new compounds were characterized by recording melting point without correction, 1H NMR, 13C NMR and elemental analysis. 2. Typical experimental procedure for the synthesis of 1c: To a stirred mixture of 4- chlorobenzaldehyde (1 mmol) and 2-hydroxynaphthoquinone (1 mmol) in ethanol (5 ml), was added L-proline (20 mol %) and the reaction mixture was stirred at reflux temperature for

30 minutes. Then 3-amino-5-methylpyrazole (1mmol) was added to it. The resulting mixture was stirred until the reaction was completed as indicated by TLC. The resulting solid was collected by filtration and washed with ethanol to afford the product. The resulting product was pure enough for characterization. S3 3. Copies of 1H and 13C NMR spectra of compounds H N NH N O O 1a H N NH N O O 1a S4 H N NH N O O F 1b H N NH N O O F 1b S5 H N NH N O O Cl 1c H N NH N O O Cl 1c S6 H N NH N O O Br 1d H N NH N O O Br 1d S7 H N NH N O O 1e H N NH N O O 1e S8 H N NH N O O NO2 1f H N NH N O O NO2 1f S9 H N NH N O O OMe 1g H N NH N O O OMe 1g S10 H N NH N O O Cl 1h H N NH N O O Cl 1h S11 H N NH N O O OH 1i H N NH N O O OH 1i S12 H N NH N O O NO2 1j H N NH N O O NO2 1j S13 H N NH N O O 1k H N NH N O O 1k S14 H N NH N O O 1l H N NH N O O 1l S15 H N NH N O O Cl Cl 1m H N NH N O O Cl Cl 1m S16 H N NH N O O OMe 1n H N NH N O O OMe 1n S17 H N NH N O O 1o H N NH N O O 1o S18 H N NH N O O O 1p H N NH N O O O 1p