Zirconyl Nitrate as an Efficient Catalyst for Facile Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1H)-one Derivatives in Aqueous ­Medium

Amarsinha Gorepatil; Pratapsinha Gorepatil; Mahadev Gaikwad; Dattakumar Mhamane; Ajit Phadkule; Vilas Ingle

doi:10.1055/s-0036-1589110

Synlett, Table of Contents

Synlett 2018; 29(02): 235-237
DOI: 10.1055/s-0036-1589110

letter

Zirconyl Nitrate as an Efficient Catalyst for Facile Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1H)-one Derivatives in Aqueous Medium

Authors

Amarsinha Gorepatil

^aDepartment of Chemistry, S. G. R. G. Shinde College, Paranda, Dist-Osmanabad (MH), 413 505, India
Pratapsinha Gorepatil

^bDepartment of Chemistry, Sangameshwar College, Solapur (MH), 413 001, India
Mahadev Gaikwad

^cDepartment of Chemistry, B. P. C. A. S. Angar, Dist- Solapur (MH), 413 214, India
Dattakumar Mhamane

^bDepartment of Chemistry, Sangameshwar College, Solapur (MH), 413 001, India
Ajit Phadkule

^bDepartment of Chemistry, Sangameshwar College, Solapur (MH), 413 001, India
Vilas Ingle*

^dDepartment of Chemistry, S. C. S. College, Omerga, Dist-Osmanabad (MH), 413 606, India Email: inglevilas71@yahoo.in

Abstract

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Abstract

A simple, green, and efficient method is introduced for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones under mild reaction conditions with improved yields by intramolecular cyclization of o-aminochalcones with zirconyl nitrate [Zn(O)(NO₃)₂·nH₂O] as a water-tolerant Lewis-acid catalyst.

Key words

zirconyl nitrate - dihydroquinolinones - aminochalcones - cyclization - Lewis acids

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References

References and Notes

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10 2-Aryl-2,3-dihydroquinolin-4(1H)-ones; General Procedure A mixture of the appropriate 2-aminochalcone (1 mmol), EtOH (2 mL), H₂O (2 mL), and ZrO(NO₃)₂·nH₂O (46 mg, 20 mol%) was heated with stirring at 50 °C while the progress of the reaction was monitored by TLC. The reaction was then quenched with H₂O (5 mL), and the mixture was extracted with Et₂O (3 × 10 mL). The combined organic extracts were washed with brine (5 mL) then dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography [silica gel, hexane–EtOAc (10:1)]. 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry 1)^5b,6b,11 Off-white solid; yield: 218 mg (98%); mp 153–155 °C. IR (KBr): 3060, 3028, 1638, 1572, 1494, 1358, 1324, 1295, 1157, 1095, 974, 861 cm^–1. ¹H NMR (600 MHz, CDCl₃): δ = 7.83 (dd, J = 8.5, 1.2 Hz, 1 H), 7.42 (d, J = 7.4 Hz, 2 H), 7.40–7.36 (m, 2 H), 7.35–7.33 (m, 2 H), 6.76 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 8.5 Hz, 1 H), 4.70 (dd, J = 13.5, 3.6 Hz, 1 H), 4.65 (s, 1 H, NH), 2.82 (dd, J = 16.3, 14.4 Hz, 1 H), 2.70 (dd, J = 15.6, 3.6 Hz, 1 H). ¹³C NMR (150 MHz, CDCl₃): δ = 192.9, 152.4, 136.1, 128.6, 128.3, 127.4, 126.5, 119.2, 117.2, 116.7, 59.1, 45.7. MS (EI): m/z = 223.10 [M⁺]. 2-(4-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (Table 2 Entry 2)^4a,11,12 Red solid; yield: 249 mg (97%); mp 168–170 °C. IR (KBr): 3343, 3210, 2980, 1666, 1585, 1221, 1150, 750 cm^–1. ¹H NMR (600 MHz, CDCl₃): δ = 7.83 (dd, J = 7.8, 1.2 Hz, 1 H), 7.38–7.31 (m, 5 H), 6.78 (t, J = 7.2 Hz, 1 H), 6.71 (d, J = 7.8 Hz, 1 H), 4.69 (dd, J = 14.5, 4.2 Hz, 1 H), 4.54 (s, 1 H, NH), 2.79 (dd, J = 17.3, 14.5 Hz, 1 H), 2.71 (dd, J = 17.3, 4.2 Hz, 1 H). ¹³C NMR (150 MHz, CDCl₃): δ = 193.5, 152.3, 138.4, 136.4, 134.1, 129.2, 127.8, 127.5, 119.2, 118.7, 115.9, 57.8, 46.3. MS (EI): m/z = 257.07 [M⁺]. 2-(4-Methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry 10)^3e,4a,13 Brown solid; yield: 250 mg (99%); mp 145–147 °C. IR (KBr): 3330, 3145, 2978, 2737, 1663, 1585, 1305, 1224, 1132cm^–1. ¹H NMR (300 MHz, CDCl₃): δ = 7.85 (dd, J = 7.8, 1.5 Hz, 1 H), 7.37–7.33 (m, 2 H), 7.31–7.28 (m, 1 H), 6.95–6.86 (m, 2 H), 6.81–6.74 (m, 1 H), 6.67 (d, J = 8.1 Hz, 1 H), 4.69 (dd, J = 13.5, 3.6 Hz, 1 H), 4.33 (s, 1 H, NH), 3.80 (s, 3 H), 2.89–2.70 (m, 2 H). ¹³C NMR (150 MHz, CDCl₃): δ = 193.3, 158.9, 152.1, 135.5, 133.2, 127.9, 127.7, 119.1, 118.4, 116.0, 114.1, 58.0, 55.5, 46.6. MS (EI): m/z = 253.10 [M⁺]. 2-(4-Bromophenyl)-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry 11)^4a,6b,12 Brown solid; yield: 290 mg (96%); mp 167–169 °C. IR (KBr): 3324, 3053, 1654, 1492, 1325, 1110, 754 cm^–1. ¹H NMR (300 MHz, CDCl₃): δ = 7.85 (dd, J = 7.8, 1.5 Hz, 1 H), 7.53–7.48 (m, 2 H), 7.36–7.30 (m, 3 H), 6.81–6.76 (m, 1 H), 6.70 (d, J = 8.2 Hz, 1 H), 4.71 (dd, J = 17.4, 4.8 Hz, 1 H), 4.44 (s, 1 H, NH), 2.87–2.77 (m, 1 H), 2.77–2.70 (m, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 193.7, 152.3, 141.3, 136.9, 132.3, 128.5, 127.8, 123.4, 119.2, 118.8, 117.1, 58.1, 47.1. MS (EI): m/z = 301.02 [M⁺].
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Zirconyl Nitrate as an Efficient Catalyst for Facile Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1H)-one Derivatives in Aqueous ­Medium

Authors

Zirconyl Nitrate as an Efficient Catalyst for Facile Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1H)-one Derivatives in Aqueous Medium