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

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2010(15): 2325-2329
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;

Further Information

Publication History

Received 3 June 2010
Publication Date:
06 August 2010 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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

References and Notes

1 Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; San Diego: 1997.

Google Scholar
Reviews:
2a Moriarty RM. Vaid RK. Synthesis 1990, 431

Google Scholar
2b Stang PJ. Angew. Chem., Int. Ed. Engl. 1992, 31: 274

Google Scholar
2c Prakash O. Saini N. Sharma PK. Synlett 1994, 221

Google Scholar
2d Kitamura T. Yuki Gosei Kagaku Kyokaishi 1995, 53: 893

Google Scholar
2e Stang PJ. Zhdankin VV. Chem. Rev. 1996, 96: 1123

Google Scholar
2f Umemoto T. Chem. Rev. 1996, 96: 1757

Google Scholar
2g Kita Y. Takada T. Tohma H. Pure Appl. Chem. 1996, 68: 627

Google Scholar
2h Togo H. Hoshina Y. Nogami G. Yokoyama M. Yuki Gosei Kagaku Kyokaishi 1997, 55: 90

Google Scholar
2i Varvoglis A. Tetrahedron 1997, 53: 1179

Google Scholar
2j Zhdankin VV. Rev. Heteroat. Chem. 1997, 17: 133

Google Scholar
2k Muraki T. Togo H. Yokoyama M. Rev. Heteroat. Chem. 1997, 17: 213

Google Scholar
2l Kitamura T. Fujiwara Y. Org. Prep. Proced. Int. 1997, 29: 409

Google Scholar
2m Varvoglis A. Spyroudis S. Synlett 1998, 221

Google Scholar
2n Zhdankin VV. Stang PJ. Tetrahedron 1998, 54: 10927

Google Scholar
2o Moriarty RM. Prakash O. Adv. Heterocycl. Chem. 1998, 69: 1

Google Scholar
2p Togo H. Katohgi M. Synlett 2001, 565

Google Scholar
2q Zhdankin VV. Stang PJ. Chem. Rev. 2002, 102: 2523

Google Scholar
2r Richardson RD. Wirth T. Angew. Chem. Int. Ed. 2006, 45: 4402

Google Scholar
2s Ladziata U. Zhdankin V. Synlett 2007, 527

Google Scholar
Review:
3a Togo H. Katohgi M. Synlett 2001, 565

Google Scholar
Recent papers:
3b Boto A. Betancor C. Suarez E. Tetrahedron Lett. 1994, 35: 5509

Google Scholar
3c Boto A. Betancor C. Suarez E. Tetrahedron Lett. 1994, 35: 6933

Google Scholar
3d Arencibia T. Salazar JA. Suarez E. Tetrahedron Lett. 1994, 35: 7463

Google Scholar
3e Hernandez R. Velazquez SM. Suarez E. Rodriguez MS. J. Org. Chem. 1994, 59: 6395

Google Scholar
3f Lee J. Oh J. Jin SJ. Choi JR. Atwood JL. Cha JK. J. Org. Chem. 1994, 59: 6955

Google Scholar
3g Boto A. Betancor C. Prange T. Suarez E. J. Org. Chem. 1994, 59: 4393

Google Scholar
3h Hernandez R. Suarez E. J. Org. Chem. 1994, 59: 2766

Google Scholar
3i Francisco CG. Freire R. Rodriguez MS. Suarez E. Tetrahedron Lett. 1995, 36: 2141

Google Scholar
3j Hernandez R. Velazquez SM. Suarez E. Tetrahedron Lett. 1996, 37: 6409

Google Scholar
3k Francisco CG. Gonzalez CC. Suarez E. Tetrahedron Lett. 1996, 37: 1687

Google Scholar
3l Hernandez R. Leon EI. Moreno P. Suarez E. J. Org. Chem. 1997, 62: 8974

Google Scholar
3m Francisco CG. Freire R. Gonzalez CC. Suarez E. Tetrahedron: Asymmetry 1997, 8: 1971

Google Scholar
3n de Armas P. García-Tellado F. Marrero-Tellado JJ. Robles J. Tetrahedron Lett. 1997, 38: 8081

Google Scholar
3o Boto A. Hernandez R. Velazquez SM. Suarez E. J. Org. Chem. 1998, 63: 4697

Google Scholar
3p Francisco CG. Martin CG. Suarez E. J. Org. Chem. 1998, 63: 8092

Google Scholar
3q Francisco CG. Martin CG. Suarez E. J. Org. Chem. 1998, 63: 2099

Google Scholar
3r Khan N. Cheng X. Mootoo DR. J. Am. Chem. Soc. 1999, 121: 4918

Google Scholar
3s Adinolfi M. Barone G. Iadonisi A. Synlett 1999, 65

Google Scholar
3t Wipf P. Mareska DA. Tetrahedron Lett. 2000, 41: 4723

Google Scholar
4a Ogata Y. Aoki K. J. Am. Chem. Soc. 1968, 90: 6187

Google Scholar
4b Merkushev EB. Simakhina ND. Koveshnikova GM. Synthesis 1980, 486

Google Scholar
5 Courtneidge JL. Lusztyk J. Page D. Tetrahedron Lett. 1994, 35: 1003

Crossref Google Scholar
6a Muraki T. Togo H. Yokoyama M. Tetrahedron Lett. 1996, 37: 2441

Google Scholar
6b Togo H. Muraki T. Hoshina Y. Yamaguchi K. Yokoyama M. J. Chem. Soc., Perkin Trans. 1 1997, 787

Google Scholar
7a Togo H. Katohgi M. Yokoyama M. Synlett 1998, 131

Google Scholar
7b Togo H. Hoshina Y. Muraki T. Nakayama H. Yokoyama M. J. Org. Chem. 1998, 63: 5193

Google Scholar
7c Katohgi M. Togo H. Yamaguchi K. Yokoyama M. Tetrahedron 1999, 55: 14885

Google Scholar
7d Togo H. Nabana T. Yokoyama M. J. Org. Chem. 2000, 65: 8391

Google Scholar
7e Togo H. Harada Y. Yokoyama M. J. Org. Chem. 2000, 65: 926

Google Scholar
8 Orazi OO. Corral RA. Bertorello HE. J. Org. Chem. 1965, 30: 1101

Crossref Google Scholar
9a Booth SE. Jenkins PR. Swain CJ. Sweeney JB. J. Chem. Soc., Perkin Trans. 1 1994, 3499

Google Scholar
9b Larock RC. Yum EK. Doty MJ. Sham KKC. J. Org. Chem. 1995, 60: 3270

Google Scholar
9c Deshpande PP. Tagliaferri F. Victory SF. Yan S. Baker DC. J. Org. Chem. 1995, 60: 2964

Google Scholar
9d Deshpande PP. Baker DC. Synthesis 1995, 707

Google Scholar
9e Kuwabe S. Torraca KE. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 12202

Google Scholar
9f Koufaki M. Detsi A. Theodorou E. Kiziridi C. Bioorg. Med. Chem. 2004, 12: 4835

Google Scholar
9g Shi Z. He C. J. Am. Chem. Soc. 2004, 126: 13596

Google Scholar
9h Niu J. Guo P. Kang J. Li Z. Xu J. Hu S. J. Org. Chem. 2009, 74: 5075

Google Scholar
9i Zhang L. Zhang W. Liu J. Hu J. J. Org. Chem. 2009, 74: 2850

Google Scholar
10a Iida S. Togo H. Synlett 2007, 407

Google Scholar
10b Iida S. Togo H. Tetrahedron 2007, 63: 8274

Google Scholar
10c Takahashi S. Togo H. Synthesis 2009, 2329

Google Scholar
10d Moroda A. Furuyama S. Togo H. Synlett 2009, 1336

Google Scholar
10e Iida S. Ohmura R. Togo H. Tetrahedron 2009, 65: 6257

Google Scholar
10f Baba H. Togo H. Tetrahedron Lett. 2010, 51: 2063

Google Scholar

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.