Operationally Simple and Selective One-Pot Synthesis of Hydroxyphenones: A Facile Access to SNARF Dyes

Celin Richter; Nikolaus P. Ernsting; Rainer Mahrwald

doi:10.1055/s-0035-1561370

Synthesis, Table of Contents

Synthesis 2016; 48(08): 1217-1225
DOI: 10.1055/s-0035-1561370

paper

Operationally Simple and Selective One-Pot Synthesis of Hydroxyphenones: A Facile Access to SNARF Dyes

Celin Richter

Department of Chemistry, Humboldt Universität zu Berlin, Brook-Taylor Str. 2, 12484 Berlin, Germany Email: rainer.mahrwald@rz.hu-berlin.de

,

Nikolaus P. Ernsting

Department of Chemistry, Humboldt Universität zu Berlin, Brook-Taylor Str. 2, 12484 Berlin, Germany Email: rainer.mahrwald@rz.hu-berlin.de

,

Rainer Mahrwald*

Department of Chemistry, Humboldt Universität zu Berlin, Brook-Taylor Str. 2, 12484 Berlin, Germany Email: rainer.mahrwald@rz.hu-berlin.de

› Author Affiliations

Abstract

All articles of this category

Abstract

High selectivity is observed during a Friedel–Crafts acylation/demethylation cascade. In contrast to this cascade, oxygen-containing acylating reagents do not undergo the demethylation step. By the methodology elaborated here, an access is provided to important intermediates for the total synthesis of seminaphthorhodafluor (SNARF) dyes.

Key words

Friedel–Crafts acylation - demethylation cascade - aluminum chloride - selectivity

Full Text

References

References
1 Han J, Burgess K. Chem. Rev. 2010; 110: 2709
2 Whitaker JE, Haugland RP, Prendergast FG. Anal. Biochem. 1991; 194: 330
3 Richter C, Schneider C, Quick M, Volz P, Mahrwald R, Hughes J, Dick B, Alexiev U, Ernsting NP. Phys. Chem. Chem. Phys. 2015; 17: 30590

4a For an overview of these synthetic procedures, see: Marsini MA, Pettus TR. R. In Science of Synthesis . Vol. 31a. Ramsden CA. Thieme; Stuttgart: 2007: 447
4b For acylation of unprotected phenols in the presence of titanium(IV) chloride, see: Bensari A, Zaveri NT. Synthesis 2003; 267
4c For acylation of phloroglucinol in the presence of boron trifluoride, see: Mateeva NN, Kode RN, Redda KK. J. Heterocycl. Chem. 2002; 39: 1251
4d Liu Q, Liu Q, Qiang X, Li Y, Sang Z, Li Y, Tan Z, Deng Y. Bioorg. Med. Chem. 2015; 23: 911
4e Yao J, Zhang B, Ge C, Peng S, Fang J. J. Agric. Food Chem. 2015; 63: 1521
4f Zhang B, Duan D, Ge C, Yao J, Liu Y, Li X, Fang J. J. Med. Chem. 2015; 58: 1795
4g Wang J, Zhou R-G, Wu T, Yang T, Qin Q-X, Li L, Yang B, Yang J. J. Chem. Res. 2012; 36: 121
4h Wei G, Yu B. Eur. J. Org. Chem. 2008; 3156
4i For acylation of phloroglucinol in the presence of AlCl₃, see: Wu L, Luo J, Zhang Y, Zhu M, Wang X, Luo J, Yang M, Yu B, Yao H, Dai Y, Guo Q, Chen Y, Sun H, Kong L. Tetrahedron Lett. 2015; 56: 229
4j Nishiwaki H, Fujiwara S, Wukirsari T, Iwamoto H, Mori S, Nishi K, Sugahara T, Yamauchi S, Shuto Y. J. Nat. Prod. 2015; 78: 43
4k Sun Q, Schmidt S, Tremmel M, Heilmann J, König B. Eur. J. Med. Chem. 2014; 85: 621
4l Tyrell E, Archer R, Tucknott M, Colston K, Pirianov G, Ramanthan D, Dhillon R, Sinclair A, Skinner GA. Phytochem. Lett. 2012; 5: 144
4m Morkunas M, Dube L, Götz F, Maier ME. Tetrahedron 2013; 69: 8559
4n Mueller H, Paul M, Hartmann D, Huch V, Blaesius D, Koeberle A, Werz O, Jauch J. Angew. Chem. Int. Ed. 2010; 49: 2045 ; and references cited therein

5 Sartori G, Casnati G, Bigi F, Predieri G. J. Org. Chem. 1990; 55: 4371

Lewis acid mediated addition of nitriles to phenols (Houben–Hoesch acylation):

6a Booth BL, Noori GF. M. J. Chem. Soc., Perkin Trans. 1 1980; 2894
6b Beck G, Bergmann A, Keßeler K, Wess G. Tetrahedron Lett. 1990; 31: 7293
6c Beutler JA, Hamel E, Vlietinck AJ, Haemers A, Rajan P, Roitman JN, Cardellina JH. II, Boyd MR. J. Med. Chem. 1998; 41: 2333
6d Bennett CJ, Caldwell ST, McPhail DB, Morrice PC, Duthie GG, Hartley RC. Bioorg. Med. Chem. 2004; 12: 2079
6e Li NG, You QD, Huang XF, Wang JX, Guo QL, Chen XG, Li Y, Li HY. Chin. Chem. Lett. 2007; 18: 659
6f Hu Y, Yang Y, Yu Y, Wen G, Shang N, Zhuang W, Lu D, Zhou B, Liang B, Yue X, Li F, Du J, Bu X. J. Med. Chem. 2013; 56: 6033
6g Liu G, Ge Z, Zhao M, Zhou Y. Molecules 2013; 18: 14070
6h Belloa ML, Chiaradiac LD, Dias LR. S, Pachecod LK, Stumpf TR, Mascarelloc A, Steindeld M, Yunesc RA, Castroe HC, Nunesc RJ, Rodrigues CR. Bioorg. Med. Chem. 2011; 19: 5046

For multistep construction of the required target molecule by the use of commercially available 4-dimethylamino-2-hydroxybenzaldehyde, see:

6i Chou P.-T, Huang C.-H, Pu S.-C, Cheng Y.-M, Liu Y.-H, Wang Y, Chen C.-T. J. Phys. Chem. A 2004; 108: 6452

For access to the corresponding substituted acylated intermediate by Fries rearrangement, see:

6j Poronik YM, Shandura MP, Kovtun YP. Dyes Pigments 2007; 72: 199
6k Cheng Y.-M, Pu S.-C, Yu Y.-C, Chou P.-T, Huang C, Chen C.-T, Li T.-H, Hu W.-P. J. Phys. Chem. A 2005; 109: 11696
6l Poronik YM, Shandura MP, Kovtun YP. Chem. Heterocycl. Compd. 2005; 41: 546
6m Sauers RR, Husain SN, Piechowski AP, Bird GR. Dyes Pigments 1987; 8: 35

7 Huang H, Zhang L, Zhang X, Ji X, Ding X, Shen X, Jiang H, Liu H. Chin. J. Chem. 2010; 28: 1041
8 Tananka T, Kumamoto T, Ishikawa T. Tetrahedron: Asymmetry 2000; 11: 4633
9 Sagrera G, Seoane G. Synthesis 2010; 2776

10a AlCl₃: Hemant VC, Laxman KA, Amol SK, Valmik DD, Vishnu NT, Babasaheb PB. J. Enzyme Inhib. Med. Chem. 2015; 30: 22
10b BCl₃: Liu M, Zhang J, Yang J, Yang B, Cui W. J. Chem. Res. 2014; 38: 134
10c BCl₃: Zhang J, Liu M, Cui W, Yang J, Yang B. J. Chem. Res. 2014; 38: 60
10d BCl₃: Zhang J, Liu M, Cui W, Yang J, Liao X-l. J. Chem. Res. 2013; 37: 694
10e AlCl₃: Chavan HV, Bandgar BP, Adsul LK, Dhakane VD, Bhale PS, Thakare VN, Masand V. Bioorg. Med. Chem. Lett. 2013; 23: 1315
10f AlCl₃: Bandgar BP, Chavan HV, Adsul LK, Thakare VN, Shringare SN, Shaikh R, Gacche RN. Bioorg. Med. Chem. Lett. 2013; 23: 912
10g AlCl₃: Adogla EA, Janser RF, Fairbanks SS, Vortolomei CM, Meka RK, Janser I. Tetrahedron Lett. 2012; 53: 11
10h AlCl₃: Bandgar BP, Patil SA, Korbad BL, Nile SH, Khobragade CN. Eur. J. Med. Chem. 2010; 45: 2629
10i AlCl₃: Bandgar BP, Patil SA, Gacche RN, Korbad BL, Hote BS, Kinkar SN, Jalde SS. Bioorg. Med. Chem. Lett. 2010; 20: 730
10j TiCl₄: Kawamoto H, Nakatsubo F, Murakami K. J. Wood Chem. Technol. 1989; 9: 35
10k AlCl₃: Dijkstra P, Van Steen B, Hams BH. M, den Hertog HJ. Jr, Reinhoudt DN. Tetrahedron Lett. 1986; 27: 3183
10l Ghosal S, Chaudhuri RK, Markham KR. J. Chem. Soc., Perkin Trans. 1 1974; 2538
10m Ghosal S, Biswas K, Chaudhuri RK. J. Chem. Soc., Perkin Trans. 1 1977; 1597

11 Auwers K. Justus Liebigs Ann. Chem. 1909; 364: 147
12 Du Z.-T, Lu J, Yu H.-R, Xu Y, Li A.-P. J. Chem. Res. 2010; 34: 222

For acylation of trimethoxybenzene in the presence of aluminum chloride without affecting the methyl ether, see:

13a Matsumoto T, Singh IP, Etoh H, Tanaka H. Chem. Lett. 2001; 210
13b Lal K, Zarate EA, Youngs WJ, Salomon RG. J. Org. Chem. 1988; 53: 3673
13c AlCl₃/dimethoxybenzene: Murakami M, Kobayashi K, Hirai K. Chem. Pharm. Bull. 2000; 48: 1567
13d SnCl₄/dimethoxybenzene: Matsubara H, Yasuda S, Ryu I. Synlett 2003; 247
13e Cat. SmI₃/dimethoxybenzene: Chen X, Yu M, Wang M. J. Chem. Res. 2005; 80
13f AlCl₃/glutaric anhydride: Kooistra FB, Knol J, Kastenberg F, Popescu LM, Verhees WJ. H, Kroon JM, Hummelen JC. Org. Lett. 2007; 9: 551
13g AlCl₃: Zhang W.-J, Wu J.-F, Zhou P.-F, Wang Y, Hou A.-J. Tetrahedron 2013; 69: 5850
13h AlCl₃/dimethoxybenzene: Grelier G, Chenard E, Büschleb M, Hanessian S. Synthesis 2015; 47: 1091
13i By deactivation of AlCl₃ with additional H₂O, the concomitant demethylation is suppressed quantitatively, see: Dijkstra PJ, Den Hertog HJ. Jr, Van Steen BJ, Zijlstra S, Skowronska-Ptasinska M, Reinhoudt DN, Van Eerden J, Harkema S. J. Org. Chem. 1987; 52: 2433

14a Asolkar RN, Kamat VP, Kirtany JK. J. Chem. Res. 2001; 549
14b Ghosal S, Mittal P, Kumar Y, Singh SK. Phytochemistry 1989; 28: 3193
14c In a comparison of the results from references 14a and 14b, both reports describe the acetylation of trimethoxybenzene in the presence of an excess of AlCl₃ under the same conditions. Asolkar et al. obtained trimethyoxyacetophenone, whereas Ghosal et al. observed the concomitant demethylation to yield the hydroxydimethoxyacetophenone under the same conditions.

15a AlCl₃/acyl halide 23: Torosyan SA, Mikheev VV, Biglova YN, Miftakhov MS. Russ. J. Org. Chem. 2015; 51: 940
15b SnCl₄/acyl halide 23: Joie C, Deckers K, Enders D. Synthesis 2014; 46: 799
15c Lee JI, Park SB. Bull. Korean Chem. Soc. 2012; 33: 1379
15d TiCl₄/acyl halide 23: Kraus GA, Gupta V, Kempena A. Synlett 2012; 23: 385
15e AlCl₃/acyl halide 23: Lowell AN, Fennie MW, Kozlowski MC. J. Org. Chem. 2008; 73: 1911
15f Yoshikawa N, Doyle A, Tan L, Murry JA, Akao A, Kawasaki M, Sato K. Org. Lett. 2007; 9: 4103
15g AlCl₃/acyl halide 23: Ianni A, Waldvogel SR. Synthesis 2006; 2103

16 Bycroft BW, Hatton JR, Roberts JC. J. Chem. Soc. 1970; 281
17 Zhang L, Zhang JY. J. Comb. Chem. 2006; 8: 361
18 Cignarella G, Barlocco D, Curzu MM, Pinna GA, Cazzulani P, Cassin M, Lumachi B. Eur. J. Med. Chem. 1990; 9: 749
19 Donnelly JA, Maloney DE. Tetrahedron 1979; 35: 2883
20 Lee H, Yi CS. Eur. J. Org. Chem. 2015; 1899
21 Bergeron RJ, Wiegand J, Weimar WR, Vinson JR. T, Bussenius J, Yao GW, McManis JS. J. Med. Chem. 1999; 42: 95
22 Venu T, Shashikanth S, Khanum S, Naveen S, Firdouse A, Sridhar M, Prasad JS. Bioorg. Med. Chem. 2007; 15: 3505
23 Fillol L, Martínez-Utrilla R, Miranda M, Morera I. Monatsh. Chem. 1989; 120: 863
24 Carpino PA, Conn EL, Hepworth D, Kung DW, Rocke BN, Ruggeri RB, Warmus JS, Zhang Y, Dow RL, Dowling MS, Orr ST. M, Sammons MF. PCT Int. Appl WO 2013068875, 2013
25 Mahmood SJ, McLaughlin M, Hossain MM. Synth. Commun. 1999; 29: 2967
26 Sandifer RM, Bhattacharya AK, Harris TM. J. Org. Chem. 1981; 46: 2260

Supplementary Material

Supporting Information