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

Firouz Matloubi Moghaddam; Vahid Saberi; Seyedmahmoudreza Keshavarz

doi:10.1055/s-0036-1591918

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CC BY ND NC 4.0 · SynOpen 2018; 02(01): 0036-0040
DOI: 10.1055/s-0036-1591918

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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

Firouz Matloubi Moghaddam *

,

Vahid Saberi

,

Seyedmahmoudreza Keshavarz

Abstract

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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

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References

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.

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