Synlett 2010(16): 2503-2505  
DOI: 10.1055/s-0030-1258568
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Diazonaphthoquinones from Naphthols by Diazo-Transfer Reaction with 2-Azido-1,3-dimethylimidazolinium Chloride

Mitsuru Kitamura*, Norifumi Tashiro, Rie Sakata, Tatsuo Okauchi
Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu-shi, Fukuoka, 804-8550, Japan
Fax: +81(93)8843304; e-Mail: kita@che.kyutech.ac.jp;
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Publikationsverlauf

Received 22 July 2010
Publikationsdatum:
14. September 2010 (online)

Abstract

An efficient synthetic method for the synthesis of diazo­naphthoquinones from naphthols is described. A variety of diazo­naphthoquinones were synthesized from the corresponding naphthols by the diazo transfer with 2-azido-1,3-dimethylimidazolinium chloride prepared by the reaction of 2-chloro-1,3-dimethylimidazorinium chloride and sodium azide.

    References and Notes

  • For a review, see:
  • 1a Ershov VV. Nikiforov GA. de Jonge CRHI. Quinone Diazides   Elsevier; Amsterdam: 1981. 
  • 1b Zollinger H. Diazo Chemistry   VCH; Weinheim: 1994. 
  • 2a Ried W. Appel H. Justus Liebigs Ann. Chem.   1961,  646:  82 
  • 2b Figueiredo LJO. Kascheres C. J. Org. Chem.  1997,  62:  1164 
  • 3 Colas C. Goeldner M. Eur. J. Org. Chem.  1999,  1357 
  • 4a Yagihara M. Kitahara Y. Asao T. Chem. Lett.  1974,  1015 
  • 4b Hacker NP. Turro NJ. Tetrahedron Lett.  1982,  23:  1771 
  • 4c Bucher G. Sander W. J. Org. Chem.  1992,  57:  1346 
  • 4d Almstead J.-IK. Urwyler B. Wirz J. J. Am. Chem. Soc.  1994,  116:  954 
  • 4e Qiao GG. Andraos J. Wentrup C. J. Am. Chem. Soc.  1996,  118:  5634 
  • 4f de Lucas NC. Netto-Ferreira JC. Andraos J. Lusztyk J. Wagner BD. Scaiano JC. Tetrahedron Lett.  1997,  38:  5147 
  • 4g Murata S. Kobayashi J. Kongou C. Miyata M. Matsushita T. Tomioka H. J. Org. Chem.  2000,  65:  6082 
  • 4h Kirmse W. Eur. J. Org. Chem.  2002,  2193 
  • 4i Urdabayev NK. Popik VV. J. Am. Chem. Soc.  2004,  126:  4058 
  • For reviews, see:
  • 5a Reiser A. Shih H.-Y. Yeh T.-F. Huang J.-P. Angew. Chem., Int. Ed. Engl.  1996,  35:  2428 
  • 5b Reiser A. Huang JP. He X. Yeh TF. Jha S. Shih HY. Kim MS. Han YK. Yan K. Eur. Polym. J.  2002,  38:  619 
  • 5c Fukukawa K.-i. Ueda M. Polym. J.  2008,  40:  281 
  • 6a Anderson LC. Roedel MJ. J. Am. Chem. Soc.  1945,  67:  955 
  • 6b Anderson JDC. Le Fevra RJW. Wilson IR. J. Chem. Soc.  1949,  2082 
  • 6c Tedder JM. Webster B. J. Chem. Soc.  1960,  4417 
  • 6d Sander W. Bucher G. Wandel H. Kraka E. Cremer D. Sheldrick WS. J. Am. Chem. Soc.  1997,  119:  10660 
  • 7a Cava MP. Litle RL. Napier DR. J. Am. Chem. Soc.  1958,  80:  2257 
  • 7b Ried W. Dietrich R. Chem. Ber.  1961,  94:  387 
  • 7c Trost BM. Kinson PL. J. Am. Chem. Soc.  1975,  97:  2438 
  • 7d Hacker NP. Turro NJ. Tetrahedron Lett.  1982,  23:  1771 
  • 7e Hacker NP. Kasai PH. J. Am. Chem. Soc.  1993,  115:  5410 
  • 7f Brown PJN. Cadogan JIG. Gosney I. Johnstone A. Paton RM. Wilson NH. J. Chem. Soc., Perkin Trans. 2  1996,  2303 
  • 7g Ferreira VF. Jorqueira A. Leal KZ. Pimentel HRX. Seidl PR. da Silva MN. da Souza MCBV. Pinto AV. Wardell JL. Wardell SMSV. Magn. Reson. Chem.  2006,  44:  481 
  • For reviews, see:
  • 8a Regitz M. Angew. Chem., Int. Ed. Engl.  1967,  6:  733 
  • 8b Regitz M. Synthesis  1972,  351 
  • 8c Doyle MP. Chem. Rev.  1986,  86:  919 
  • 8d Padwa A. Austin DJ. Angew. Chem., Int. Ed. Engl.  1994,  33:  1797 
  • 8e Ye T. McKervey MA. Chem. Rev.  1994,  94:  1091 
  • 8f Doyle MP. Ye T. McKervey MA. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds   John Wiley and Sons; New York: 1998. 
  • 8g Zhang Z. Wang J. Tetrahedron  2008,  64:  6577 
  • 9 Balli H. Müller V. Sezen-Gezgin A. Helv. Chim. Acta  1978,  61:  104 
  • 10 Kitamura M. Tashiro N. Okauchi T. Synlett  2009,  2943 
  • Selected synthesis of 1-diazo-2(1H)naphthalenone (3) and 2-diazo-1(2H)naphthalenone (5), see ref. 6, 7, and 9, and also see:
  • 11a Bamberger E. Ber. Dtsch. Chem. Ges.  1894,  27:  679 
  • 11b Süs O. Glos M. Möller K. Eberhardt H.-D. Justus Liebigs Ann. Chem.  1953,  583:  150 
12

Typical Procedure for the Preparation of 1-Diazo-2(1 H )naphthalenone (3)
[Caution: Although we have never had any trouble with azidoimidazolinium salt 4, it is potentially explosive.]
To a solution of 2-chloro-1,3-dimethylimidazolinium chloride (228 mg, 1.35 mmol) in MeCN (2 mL), NaN3 (99.4 mg, 1.5 mmol), and 15-crown-5 ether (0.06 mL, 0.3 mmol) was added at -20 ˚C, and the mixture was stirred for 30 min. 2-Naphthol (130 mg, 0.90 mmol) and Et3N (0.25 mL, 1.8 mmol) in THF (4 mL) was added to the mixture, which was stirred for 20 min. The reaction was quenched with H2O, and organic materials were extracted three times with CH2Cl2. The combined extracts were washed with H2O and brine, and then, dried over anhyd Na2SO4. The solvent was removed in vacuo to afford crude compounds. The crude materials were purified by flash column chromatography (silica gel: hexane-EtOAc = 4:1) to give diazonaphthoquinone 3 in 86% yield.

13

Spectral Data for 3
IR (ATR): 2333, 2221, 2084, 1616, 1558, 1479, 1452, 1394, 1346, 1304, 1251, 1203, 819, 613 cm. ¹H NMR (400 MHz, CDCl3): δ = 7.62 (d, 1 H, J = 9.8 Hz) 7.57 (dd, 1 H, J = 7.8, 1.2 Hz) 7.51 (ddd, 1 H, J = 7.8, 7.8, 1.2 Hz), 7.28 (br d, 1 H, J = 7.8 Hz), 7.27 (ddd, J = 7.8, 7.8, 1.2 Hz), 6.65 (d, 1 H, J = 9.8 Hz). ¹³C NMR (100 MHz, CDCl3): δ = 180.2, 140.2, 130.0, 129.7, 127.1, 125.9, 125.6, 124.7, 119.6, 77.2. Anal. Calcd (%) for C10H6N2O: C, 70.58; H, 3.55; N, 16.46. Found: C, 70.76; H, 3.70; N, 16.39. Mp 74-75 ˚C (dec.).

14

Spectral Data for 5
IR (ATR): 2917, 2850, 2348, 2113, 1689, 1619, 1562 cm. ¹H NMR (400 MHz, CDCl3): δ = 8.33 (d, 1 H, J = 8.0 Hz) 7.59 (ddd, 1 H, J = 8.0, 7.2, 1.4 Hz), 7.49 (d, 1 H, J = 7.2 Hz), 7.47 (ddd, 1 H, J = 8.0, 7.2, 1.4 Hz), 6.89 (d, 1 H, J = 9.3 Hz), 6.58 (d, 1 H, J = 9.3 Hz). ¹³C NMR (100 MHz, CDCl3): δ = 180.2, 137.47, 132.6, 129.5, 128.2, 127.2, 125.3, 117.3, 116.2, 74.2. Anal. Calcd (%) for C10H6N2O: C, 70.58; H, 3.55; N, 16.46. Found: C, 70.20; H, 3.68; N, 16.74. Mp 73.5-74 ˚C (dec.).