Iodine as a New Catalyst for the Condensation of 2-Hydroxy-2,2′-bisindan-1,1′,3,3′-tetrone with Cyclic Enaminones: Synthesis of Spiro-dihydropyridine Derivatives under Acid-Free Conditions

Abstract

Iodine has been used as a new catalyst for the synthesis of spiro-dihydropyridine derivatives by the condensation of cyclic enaminones and 2-hydroxy-2,2^′-bisindan-1,1′,3,3′-tetrone.

Key words

iodine - aminouracil - spiro-dihydropyridine

• References

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• 25 Typical procedure for the synthesis of spiro-dihydropyridines 3a–j: A mixture of 2-hydroxy-2,2′-bisindan-1,1′,3,3′-tetrone 1 (1 mmol), cyclic enaminone 2a–f (1 mmol) and molecular iodine (20 mol%) in DMSO (4 mL) was stirred at 100 °C for 4 h. After completion of the reaction (monitored by TLC, ethyl acetate/n-hexane, 1:2) the reaction mixture was allowed to cool to room temperature. Water was added and the precipitate was filtered off and washed with acetone to give the product 3a–j.
• 26 Synthesis of 2-hydroxy-2,2′-bisindan-1,1′,3,3′-tetrone 1: A mixture of 1,3-indandione (10 mmol), ninhydrin (10 mmol), and triethylamine (1 mmol) in EtOH (50 mL) was stirred at room temperature for 5 h. The precipitate was filtered and washed with EtOH (2 × 5 mL) to give 1. Yellow powder; mp 187–190 °C; ¹H NMR (500 MHz, CDCl₃): δ = 8.00–7.93 (m, 2 H, Ar), 7.92–7.83 (m, 6 H, Ar), 5.47 (s, 1 H, OH), 3.96 (s, 1 H, CH); ¹³C NMR (125 MHz, CDCl₃): δ = 197, 196, 142, 141, 137, 136, 124, 124, 76, 53. Analytical data for spiro[indene-2,5′-indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidine]-1,2′,3,4′,6′(1′H,3′H,11′H)-pentaone (3a): Yield: 0.361 g (91%); red powder; mp 212–215 °C (dec.); IR (KBr): 3249, 2917, 1710, 1690, 1666 cm^–1; ¹H NMR (500 MHz, D₂O): δ = 7.89–7.85 (m, 4 H, Ar-H), 7.36 (d, J = 6.9 Hz, 1 H, Ar-H), 7.24–7.17 (m, 2 H, Ar-H), 7.00 (d, J = 6.9 Hz, 1 H, Ar-H); ¹³C NMR (125 MHz, D₂O): δ = 209, 187, 173, 170, 165, 162, 141, 138, 137, 136, 131, 130, 122, 119, 119, 100, 92, 56; Anal. Calcd for C₂₂H₁₁N₃O₅: C, 66.50; H, 2.79; N, 10.58. Found: C, 65.90; H, 2.81; N, 10.61; HRMS: m/z [M+H]⁺ calcd. for C₂₂H₁₁N₃O₅: 398.0777; found: 398.0775.