An Efficient Preparation of
Chroman Derivatives from 3-Aryl-1-propanols and Related Compounds
with 1,3-Diiodo-5,5-dimethylhydantoin under Irradiation
Conditions

Shusuke Furuyama; Hideo Togo

doi:10.1055/s-0030-1258017

LETTER

An Efficient Preparation of Chroman Derivatives from 3-Aryl-1-propanols and Related Compounds with 1,3-Diiodo-5,5-dimethylhydantoin under Irradiation Conditions

Shusuke Furuyama, Hideo Togo*
Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
e-Mail: togo@faculty.chiba-u.jp;

Abstract

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Abstract

Treatment of various 3-aryl-1-propanols with 1,3-diiodo-5,5-dimethylhydantoin (DIH) in ethyl acetate or 1,2-dichloroethane under irradiation with a tungsten lamp gave the corresponding chroman derivatives in good to moderate yields.

The present reaction proceeds via the initial formation of an alkoxyl radical and the radical cyclization onto the aromatic ring, followed by the oxidation of the formed radical intermediate with DIH to provide the chroman derivative. The same treatment of o-biphenyldimethylcarbinol, o-phenylbenzoic acid, and o-alkylbenzoic acids with DIH provided the corresponding chroman derivatives and lactone derivatives in good yields, respectively.

Key words

1,3-diiodo-5,5-dimethylhydantoin - 3-aryl-1-propanol - chroman - alkoxyl radical - cyclization - aroyloxyl radical

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Referenzen

References and Notes

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11

Typical Procedure for Preparation of Chromane from 3-Phenyl-1-propanol with DIH 1,2-Dichloroethane (15 mL) was added to the mixture of
3-phenyl-1-propanol (1.0 mmol, 136.2 mg) and DIH (1.6 mmol, 607.8 mg, commercially available from Tokyo Kasei Co.). The mixture was irradiated with a tungsten lamp (300 W) at 40 ˚C for 9 h under an argon atmosphere. After the reaction, the mixture was poured into a sat. aq Na₂SO₄ solution and extracted with CHCl₃ (3 × 15 mL). The organic layer was dried over Na₂SO₄. After filtration, the solvent was removed under reduced pressure, and the residue was treated with flash column chromatography on silica gel using a mixture of hexane and EtOAc (1: 5) as an eluent to provide chroman and 6-iodochroman.
Chromane
Oil. IR (neat): 2935, 2861, 1581, 1488, 1227, 1115 cm^-¹. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 1.98-2.04 (m, 2 H), 2.79 (t, J = 6.5 Hz, 2 H), 4.18 (t, J = 5.2 Hz, 2 H), 6.78 (d, J = 8.1 Hz, 1 H), 6.83 (dd, J = 8.1, 7.5 Hz, 1 H), 7.03 (d, J = 7.5 Hz, 1 H), 7.08 (dd, J = 7.5, 8.1 Hz, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 22.46 (s), 24.96 (s), 66.51 (s), 116.78 (t), 120.18 (t), 122.31 (q), 127.28 (t), 129.90 (t), 154.97 (q). HRMS (APPI): m/z calcd for C₉H₁₀O [M]: 134.0732; found [M⁺]: 134.0726.
6-Iodochromane Oil. IR (neat): 2900, 2850, 1560, 1480, 1230, 1120, 810 cm^-¹. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 1.97 (tt, J = 6.4, 5.1 Hz, 2 H), 2.74 (t, J = 6.4 Hz, 2 H), 4.16 (t, J = 5.1 Hz, 2 H), 6.56 (d, J = 9.2 Hz, 1 H), 7.33 (d, J = 9.2 Hz, 1 H), 7.34 (s, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 21.87 (s), 24.53 (s), 66.40 (s), 81.99 (q), 119.01 (t), 124.99 (q), 135.91 (t), 138.21 (t), 154.79 (q). HRMS (EI): m/z calcd for C₉H₉OI [M]: 259.9698; found [M⁺]: 259.9689.
2-Methyl-6-iodochromane Mp 43.0-44.0 ˚C. IR (neat): 2920, 1550, 1460, 1240, 1110, 820 cm^-¹. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 1.38 (dd, J = 6.2, 2.9 Hz, 3 H), 1.63-1.73 (m, 1 H), 1.97 (ddd, J = 13.5, 7.5, 2.9 Hz, 1 H), 2.67-2.85 (m, 2 H), 4.07-4.13 (m, 1 H), 6.56 (d, J = 8.0 Hz, 1 H), 7.34 (d, J = 8.0 Hz, 1 H), 7.35 (s, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 21.20 (p), 24.50 (s), 28.72 (s), 72.32 (t), 81.85 (q), 119.01 (t), 124.64 (q), 135.88 (t), 137.98 (t), 154.95 (q). HRMS (EI): m/z calcd for C₁₀H₁₁OI [M]: 273.9855; found [M⁺]: 273.9840.
2-Ethylchromane Oil. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 1.04 (t, J = 7.5 Hz, 3 H), 1.62-1.82 (m, 3H), 1.97-2.02 (m, 1 H), 2.75 (ddd, J = 16.3, 5.7, 3.1 Hz, 1 H), 2.84 (ddd, J = 16.3, 11.3, 6.1 Hz, 1 H), 3.88-3.94 (m, 1 H), 6.80 (d, J = 7.9 Hz, 1 H), 6.81 (dd, J = 7.9, 7.4 Hz, 1 H), 7.03 (d, J = 7.4 Hz, 1 H), 7.07 (dd, J = 7.9, 7.4 Hz, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 9.65 (p), 24.80 (s), 26.84 (s), 28.28 (s), 77.16 (t), 116.70 (t), 119.84 (t), 122.10 (q), 127.10 (t), 129.48 (t), 155.11 (q). HRMS (APCI): m/z calcd for C₁₁H₁₄O [M] 162.1039; found [M⁺]: 162.1040. 2-Ethyl-6-iodochromane Oil. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 1.03 (t, J = 7.4 Hz, 3 H), 1.59-1.82 (m, 3 H), 1.94-2.00 (m, 1 H), 2.70 (ddd, J = 16.6, 5.2, 3.4 Hz, 1 H), 2.75-2.83 (m, 1 H), 3.85-3.91 (m, 1 H), 6.57 (d, J = 8.0 Hz, 1 H), 7.33 (d, J = 8.6 Hz, 1 H), 7.34 (s, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 9.71 (p), 24.58 (s), 26.50 (s), 28.26 (s), 77.45 (t), 81.82 (q), 119.16 (t), 125.06 (q), 135.96 (t), 138.06 (t), 155.15 (q). HRMS (APCI): m/z calcd for C₁₁H₁₃OI [M]: 288.0006; found [M⁺]: 288.0005. 2-Butyl-6-iodochromane Oil. IR (neat): 2900, 2830, 1560, 1470, 1240, 1120, 820 cm^-¹. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 0.92 (t, J = 7.1 Hz, 3 H), 1.32-2.00 (m, 8 H), 2.70 (ddd, J = 16.7, 5.5, 3.3 Hz, 1 H), 2.79 (ddd, J = 16.7, 10.6, 5.1 Hz, 1 H), 3.94 (tdd, J = 10.3, 5.5, 2.2 Hz, 1 H), 6.56 (d, J = 8.2 Hz, 1 H), 7.33 (d, J = 8.2 Hz, 1 H), 7.34 (s, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 14.04 (p), 22.65 (s), 24.46 (s), 26.87 (s), 27.39 (s), 34.92 (s), 76.11 (t), 81.71 (q), 119.05 (t), 124.93 (q), 135.82 (t), 137.94 (t), 155.00 (q). HRMS (EI): m/z calcd for C₁₃H₁₇OI [M]: 316.0324; found [M⁺]: 316.0323.
2,2-Dimethyl-6-iodochromane Oil. IR (neat): 2950, 2900, 1560, 1470, 1260, 1220, 1160, 1120, 820 cm^-¹. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 1.31 (s, 6 H), 1.77 (t, J = 6.6 Hz, 2 H), 2.73 (t, J = 6.6 Hz, 2 H), 6.54 (d, J = 8.6 Hz, 1 H), 7.34 (d, J = 8.6 Hz, 1 H), 7.34 (s, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 22.14 (s), 26.75 (p), 32.34 (s), 74.50 (q), 81.44 (q), 119.60 (t), 123.79 (q), 135.99 (t), 137.91 (t), 153.96 (q). HRMS (EI): m/z calcd for C₁₁H₁₃OI [M]: 288.0011; found [M⁺]: 288.0027.
7-Methyl-6-iodochromane Oil. H NMR (400 MHz, CDCl₃, TMS): δ = 1.93-1.98 (m, 2 H), 2.32 (s, 3 H), 2.71 (t, J = 6.4 Hz, 2 H), 4.14 (t, J = 5.1 Hz, 2 H), 6.69 (s, 1 H), 7.44 (s, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 22.09 (s), 24.06 (s), 27.56 (p), 66.43 (s), 89.03 (q), 118.01 (t), 122.12 (q), 139.31 (t), 140.00 (q), 155.08 (q).
3,4-Benzocoumarin Mp 91.0-92.0 ˚C. IR (KBr): 1720, 1600, 1480, 1300, 1205, 1100, 900, 760, 730 cm^-¹. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 7.31-7.36 (m, 2 H), 7.47 (t, J = 7.7 Hz, 1 H), 7.57 (t, J = 8.0 Hz, 1 H), 7.81 (t, J = 8.0 Hz, 1 H), 8.04 (d, J = 7.7 Hz, 1 H), 8.10 (d, J = 8.0 Hz, 1 H), 8.39 (d, J = 8.0 Hz, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 117.75 (t), 118.02 (q), 121.23 (q), 121.67 (t), 122.76 (t), 124.54 (t), 128.86 (t), 130.42 (t), 130.54 (t), 134.74 (q), 134.83 (t), 151.27 (q), 161.16 (q). HRMS-FAB: m/z calcd for C₁₃H₉O₂ [M + H]: 197.0603; found [M + H]⁺: 197.0610.
3-Methylphthalide Oil. IR (neat): 2940, 1740, 1590, 1450, 1210, 1030, 760, 740 cm^-¹. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 1.64 (d, J = 6.5 Hz, 3 H), 5.57 (q, J = 6.5 Hz, 1 H), 7.64 (d, J = 7.7 Hz, 1 H), 7.53 (t, J = 7.7 Hz, 1 H), 7.68 (t, J = 7.7 Hz, 1 H), 7.89 (d, J = 7.7 Hz, 1 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 20.39 (p), 77.76 (t), 121.59 (t), 125.65 (t), 125.75 (q), 129.07 (t), 134.09 (t), 151.21 (q). HRMS-FAB: m/z calcd for C₉H₉O₂ [M + H]: 149.0603; found [M + H]⁺: 149.0627.
3-Phenylphthalide Mp 113.0-114.0 ˚C. IR (KBr): 3000, 1740, 1580, 1455, 1280, 1060, 970, 740 cm^-¹. ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 6.41 (s, 1 H), 7.27-7.40 (m, 6 H), 7.56 (t, J = 7.3 Hz, 1 H), 7.65 (t, J = 7.3 Hz, 1 H), 7.97 (d, J = 7.3 Hz, 1 H). HRMS (EI): m/z calcd for C₁₄H₁₀O₂ [M]: 210.0680; found [M⁺]: 210.0678.
6,6-Dimethyl-6 H -dibenzo[ b , d ]pyran Oil. ^¹H NMR (400 MHz, CDCl₃): δ = 1.64 (s, 6 H), 6.95 (d, J = 8.2 Hz, 1 H), 7.02 (t, J = 7.5 Hz, 1 H), 7.20-7.36 (m, 4 H), 7.70-7.75 (m, 2 H). ^¹³C NMR (100 MHz, CDCl₃, TMS): δ = 27.68 (p), 77.63 (q), 118.15 (t), 121.62 (t), 122.32 (t), 122.57 (q), 122.97 (t), 123.30 (t), 127.79 (t), 128.04 (t), 128.69 (q), 129.52 (t), 139.61 (q), 152.85 (q). HRMS (APCI): m/z calcd for C₁₅H₁₄O [M]: 210.1045; found [M⁺]: 210.1043.