Rediscovering the Double Friedel–Crafts Acylation: An Expedient Entry to Phenanthrene-9,10-diones

Nicoletta Crosta; Sebastian Müller; Dietmar Gradl; Kye-Simeon Masters; Stefan Bräse

doi:10.1055/s-0032-1318481

Synlett, Table of Contents

Synlett 2013; 24(8): 951-954
DOI: 10.1055/s-0032-1318481

letter

Rediscovering the Double Friedel–Crafts Acylation: An Expedient Entry to Phenanthrene-9,10-diones

Nicoletta Crosta

^aInstitute of Organic Chemistry (IOC), Karlsruher Institute of Technology (KIT), Fritz-Haber-Weg 6, Campus Süd, Geb. 30.42, 76131 Karlsruhe, Germany Fax: +49(721)60848581 Email: kye.masters@kit.edu Email: stefan.braese@kit.edu

,

Sebastian Müller

^aInstitute of Organic Chemistry (IOC), Karlsruher Institute of Technology (KIT), Fritz-Haber-Weg 6, Campus Süd, Geb. 30.42, 76131 Karlsruhe, Germany Fax: +49(721)60848581 Email: kye.masters@kit.edu Email: stefan.braese@kit.edu

,

Dietmar Gradl

^bZoological Institute, Cell and Developmental Biology, Karlsruhe Institute of Technology, 76131 Karlsruhe, Germany

,

Kye-Simeon Masters*

^aInstitute of Organic Chemistry (IOC), Karlsruher Institute of Technology (KIT), Fritz-Haber-Weg 6, Campus Süd, Geb. 30.42, 76131 Karlsruhe, Germany Fax: +49(721)60848581 Email: kye.masters@kit.edu Email: stefan.braese@kit.edu

^cSchool of Chemistry, Physics and Mechanical Engineering, Faculty of Science and Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia

,

Stefan Bräse*

^aInstitute of Organic Chemistry (IOC), Karlsruher Institute of Technology (KIT), Fritz-Haber-Weg 6, Campus Süd, Geb. 30.42, 76131 Karlsruhe, Germany Fax: +49(721)60848581 Email: kye.masters@kit.edu Email: stefan.braese@kit.edu

› Author Affiliations

Abstract

All articles of this category

Abstract

The double Friedel–Crafts acylation of readily accessible biaryls with oxalyl chloride delivers the respective phenanthrene-9,10-diones, providing an alternative to the traditional methods, which require harsh oxidizing conditions and multistep sequences. This simple method allows the synthesis of various symmetrical and non-symmetrical targets, and is even effective for the synthesis of the parent ring system from (unactivated) biphenyl.

Key words

cyclization - electrophilic aromatic - substitution - fused-ring systems - Friedel–Crafts acylation - phenanthrene-9,10-diones

Full Text

References

References and Notes
1 Liebermann C. Chem. Ber. 1911; 44: 1453

2a Gould SJ, Melville CR, Chen J. Tetrahedron 1997; 33: 4561
2b Sato Y, Kohnert R, Gould SJ. Tetrahedron Lett. 1986; 27: 143
2c Takagi M, Yamazaki H, Okada T, Takeda U, Sasaki T, Sezaki M, Miyaji S, Kojima M. Jpn. Patent JP 62307359, 1987 ; Chem. Abstr. 1987, 107, 76091d
2d Takagi M, Shimizu T, Okada T, Takeda U, Sasaki T, Miyado S, Shomura T, Sezaki M, Kojima M. Meiji Seika Kenkyu Nenpo 1985; 32 ; Chem. Abstr. 1985, 106, 152652j
2e Chu M, Mierzwa R, Truumees I, King A, Patel M, Berrie R, Hart A, Butkiewicz N, DasMahapatra B, Chan T.-M, Puar MS. Tetrahedron Lett. 1996; 37: 7229
2f Lepourcelet M, Chen YN, France DS, Wang H, Crews F, Petersen F, Bruseo C, Wood AW, Shivdasani RA. Cancer Cell 2004; 5: 91

3a Barker N, Clevers H. Nature Rev. Drug Discov. 2006; 5: 997
3b Huang AS, Mishina YM, Liu S, Cheung A, Stegmeier F, Michaud GA, Charlat O, Wiellette E, Zhang Y, Wiessner S, Hild M, Shi X, Wilson CJ, Mickanin C, Myer V, Fazal A, Tomlinson R, Serluca F, Shao W, Cheng H, Shultz M, Rau C, Schirle M, Schlegl J, Ghidelli S, Fawell S, Lu C, Curtis D, Kirschner MW, Lengauer C, Finan PM, Tallarico JA, Bouwmeester T, Porter JA, Bauer A, Cong F. Nature (London) 2009; 461: 614

Murrayquinone analogues:

4a Johnson BC, Polonsky J, Cohen P, Lederer E. Nature (London) 1963; 199: 285
4b Cresp TM, Giles CF, Sargent MV. J. Chem. Soc., Chem. Commun. 1974; 11
4c Jokela R, Lounasmaa M. Planta Med. 1997; 63: 85
4d Krone B, Hinrichs H, Zeeck A. J. Antibiotics 1981; 23: 1538
4e Ewersmeyer-Wenk B, Zähner H, Krone B, Zeeck A. J. Antibiotics 1981; 34: 1531
4f Krivoshchekova OE, Stepanenko LS, Mishshenko NP, Denisenko VA, Maksimov OB. Khim. Prir. Soedin. 1983; 283
4g De Pava A, Nasini G, De Pava OV. Phytochemistry 1991; 30: 2729
4h Tene M, Tane P, Tamokou Jde D, Kuiate J.-R, Connolly JD. Phytochem. Lett. 2008; 1: 120
4i Zhang J, Li L, Xiao YQ, Li W, Yin XJ, Tian GF, Chen DD, Wang Y. Chin. Chem. Lett. 2010; 21: 816

5a Gosselin F, Lau S, Nadeau C, Trinh T, O’Shea PD, Davies IW. J. Org. Chem. 2009; 74: 7790
5b Pyle AM, Rehmann JP, Meshoyrer R, Kumar CV, Turro NJ, Barton JK. J. Am. Chem. Soc. 1989; 111: 3051
5c Sitlani A, Barton JK. Biochemistry 1994; 33: 12100
5d Sitlani A, Long EC, Pyle AM, Barton JK. J. Am. Chem. Soc. 1992; 114: 2303
5e Fitzsimons MP, Barton JK. J. Am. Chem. Soc. 1997; 119: 3379

6a Echavarren AM, Porcel S In Science of Synthesis . Vol. 28. Danheiser RL, Giesbeck AG. Thieme Verlag; Stuttgart: 2006: 507 ; and references therein
6b von Anschütz R, Schultz G. Justus Liebigs Ann. Chem. 1879; 196: 32
6c Oyster L, Adkins H. J. Am. Chem. Soc. 1921; 43: 208
6d Mayer F. Chem. Ber. 1912; 45: 1105
6e Mohr B, Enkelmann V, Wegner G. J. Org. Chem. 1994; 59: 635
6f Tamarkin D, Rabinovitz M. J. Org. Chem. 1987; 52: 3472
6g Limanto J, Dorner BT, Hartner FW, Tan L. Org. Process Res. Dev. 2008; 12: 1269
6h Yoshikawa N, Doyle A, Tan L, Murry JA, Akao A, Kawasaki M, Sato K. Org. Lett. 2007; 9: 4103
6i For an innovative new approach, see: Trosien S, Waldvogel SR. Org. Lett. 2012; 14: 2976

7 Yamamoto Y, Suzuki R, Hattori K, Nishiyama H. Synlett 2006; 1027
8 Jensen FR, Goldman G. Friedel-Crafts and Related Reactions . Vol. III. Olah G. Chap. XXXVI Wiley-Interscience; New York: 1964
9 Campbell N, Scott AH. J. Chem. Soc. C 1966; 1050
10 Carey SA, Sundberg RJ. Advanced Organic Chemistry . 3rd Ed. Plenum Press; New York: 1990: Chap. 11
11 Roberts RM. G, Sardi AR. Tetrahedron 1983; 39: 137
12 For a full evaluation of the biological activity of selected phenanthrenediones, see: Halbedl S, Kratzer M.-C, Rahm K, Crosta N, Masters K.-S, Bräse S, Gradl D. FEBS Lett. 2013; 587: 522

13a Rodriguez CE, Fukuto JM, Taguchi K, Froines J, Cho AK. Chemico-Biolog. Interact. 2005; 155: 97
13b Wang Q, Dubé D, Friesen RW, LeRiche TG, Bateman KP, Trimble L, Sanghara J, Pollex R, Ramachandran C, Gresser MJ, Huang Z. Biochemistry 2004; 43: 4294
13c Urbanek RA, Suchard SJ, Steelman GB, Knappenberger KS, Sygowski LA. J. Med. Chem. 2001; 44: 1777
13d Shimada H, Oginuma M, Hara A, Imamura Y. Chem. Res. Toxicol. 2004; 17: 1145

14 Veale CA, Chapdelaine MJ, Silver SL, Lowry A. J. Am. Chem. Soc. 1934; 56: 2429
15 Typical Procedure: 3,3′-Dimethoxybiphenyl (100 mg, 0.47 mmol) was added to a solution of oxalyl chloride (0.47 mmol) in CH₂Cl₂ (7 mL). Anhyd AlCl₃ (1,4 mmol) was added in one portion and the resulting solution became black. It was stirred at r.t. for 24 h. Then the reaction mixture was poured into a mixture of H₂O (7 mL)/6 N HCl (3 mL), stirred for 15 min and then extracted with CH₂Cl₂ (2 ×). Recombined organic layers were dried (Na₂SO₄) and concentrated. Thereafter the residue was purified by silica gel chromatography (petroleum ether–EtOAc, 3:2) to afford 23b as a yellow-orange powder (37%); mp 132 °C. ¹H NMR (400 MHz, CDCl₃): δ = 7.71 (d, J = 8.0 Hz, 1 H), 7.45 (dd, J = 8.0, 8.0 Hz, 1 H), 7.30 (m, 2 H), 7.20 (dd, J = 8.0, 1.3 Hz, 1 H), 7.0 (dd, J = 8.0, 1.3 Hz, 1 H), 3.95 (s, 3 H), 3.85 (s, 3 H). ¹³C NMR (100.6 MHz, CDCl₃): δ = 194.5 (2 × C), 160.0 (2 × C), 158.7 (C), 145.6 (C), 142.0 (C), 131.0 (CH), 129.9 (CH), 129.1 (C), 119.7 (CH), 119.3 (CH), 113.2 (CH), 110.4 (CH), 55.98, 55.43.