Synthesis of Aliphatic Hydroxyaryl Ketones or (Hetero)aryl Hydroxyaryl Ketones by Acylation of Organometallic Reagents

Alan R. Katritzky; Khanh N. B. Le; Prabhu P. Mohapatra

doi:10.1055/s-2007-990786

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-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2007(20): 3141-3146
DOI: 10.1055/s-2007-990786

PAPER

Synthesis of Aliphatic Hydroxyaryl Ketones or (Hetero)aryl Hydroxyaryl Ketones by Acylation of Organometallic Reagents

Alan R. Katritzky*, Khanh N. B. Le, Prabhu P. Mohapatra
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;

Further Information

Publication History

Received 27 April 2007
Publication Date:
21 September 2007 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Diverse hydroxyarenecarboxylic acids afford stable N-(hydroxyaroyl)benzotriazoles that react with heteroaryl, alkyl, and aryl Grignard or lithium reagents to give the corresponding hydroxyaryl ketones in 51-94% yields.

Key words

hydroxyarenecarboxylic acids - N-(hydroxyaroyl)benzotriazoles - Grignard reagents - lithium - hydroxyaryl ketones

References

1 Kotali A. Harris PA. Org. Prep. Proced. Int. 1994, 26: 159

Crossref Google Scholar
2a Smith J. Thomson RH. J. Chem. Soc. 1960, 346

Crossref Google Scholar
2b Choudary BM. Ranganath KVS. Yadav J. Kantam ML. Tetrahedron Lett. 2005, 46: 1369

Crossref Google Scholar
3 Dao TT. Chi YS. Kim HP. Kim S. Park H. Bioorg. Med. Chem. Lett. 2004, 14: 1165

Crossref Google Scholar
4 . Jain PK. Grover SK. Gazz. Chim. Ital. 1984, 114: 355

Google Scholar
5 Zhang L. Zhang JY. J. Comb. Chem. 2006, 8: 361

Crossref Google Scholar
6 Breitenlechner CB. Friebe W.-G. Brunet E. Werner G. Graul K. Thomas U. Kunkele K.-P. Schafer W. Gassel M. Bossemeyer D. Huber R. Engh RA. Masjost B. J. Med. Chem. 2005, 48: 163

Crossref Google Scholar
7 Takada Y. Aggarwal BB. J. Biol. Chem. 2004, 279: 4750

Crossref Google Scholar
8 Arad D, and Elias Y. inventors; WO 9,930,699. ; Chem. Abstr. 1999, 131, 58409
9 Merza J. Aumond M.-C. Rondeau D. Dumontet V. Le Ray A.-M. Seraphin D. Richomme P. Phytochemistry 2004, 65: 2915

Crossref Google Scholar
10 Denieul MP. Laursen B. Hazell R. Skrydstrup T. J. Org. Chem. 2000, 65: 6052

Crossref Google Scholar
11 Zhu L. Cao X. Chen W. Zhang G. Sun D. Wang PG. Bioorg. Med. Chem. 2005, 13: 6381

Crossref Google Scholar
12 Stiefel CW. inventors; US 2006,239,944. 2006; Chem. Abstr. 2006, 145, 460503
13 Deckner GE. inventors; US 4,781,914. ; Chem. Abstr. 1988, 111, 120630
14 Patel M. Jain SK. Yadav AK. Gogna D. Agrawal GP. Drug Delivery 2006, 13: 323

Crossref Google Scholar
15 Harichian B, Rosa JG, and Bajor JS. inventors; US 2006,210,497. ; Chem. Abstr. 2006, 145, 362872
16 Tamarkin D, Friedman D, and Eini M. inventors; US 2006,193,789. ; Chem. Abstr. 2006, 145, 298800
17a Naeimi H. Moradi L. Catal. Commun. 2006, 7: 1067

Crossref Google Scholar
17b Naeimi H. Moradi L. J. Mol. Catal. A: Chem. 2006, 256: 242

Crossref Google Scholar
17c Dehmlow H. Aebi JD. Jolidon S. Ji Y.-H. von der Mark EM. Himber J. Morand OH. J. Med. Chem. 2003, 46: 3354

Crossref Google Scholar
17d Bensari A. Zaveri NT. Synthesis 2003, 267

Crossref Google Scholar
17e Piccolo O. Filippini L. Tinucci L. Valoti E. Citterio A. Tetrahedron 1986, 42: 885

Crossref Google Scholar
18a Ollevier T. Desyroy V. Asim M. Brochu M.-C. Synlett 2004, 2794

Crossref Google Scholar
18b Rozenberg V. Danilova T. Sergeeva E. Vorontzov E. Starikova Z. Lysenko K. Belokon Y. Eur. J. Org. Chem. 2000, 3295

Crossref Google Scholar
18c Sharghi H. Kaboudin B. J. Chem. Res., Synop. 1998, 628

Crossref Google Scholar
18d Kobayashi S. Moriwaki M. Hachiya I. Bull. Chem. Soc. Jpn. 1997, 70: 267

Crossref Google Scholar
18e Harroweven DC. Dainty RF. Tetrahedron Lett. 1996, 37: 7659

Crossref Google Scholar
18f Martin R. Org. Prep. Proced. Int. 1992, 24: 369

Crossref Google Scholar
19 Aldabbagh F. Comprehensive Organic Functional Group Transformations II Vol. 5: Katritzky AR. Taylor RJK. Elsevier; Oxford: 2005. p.1

Google Scholar
20 Xia M. Chen Z. Synth. Commun. 2000, 30: 531

Crossref Google Scholar
21 Motherwell WB. Vazqez S. Tetrahedron Lett. 2000, 41: 9667

Crossref Google Scholar
22a Katritzky AR. Suzuki K. Wang Z. Synlett 2005, 1656

Google Scholar
22b Katritzky AR. Zhang Y. Singh SK. Synthesis 2003, 2795

Google Scholar
22c Katritzky AR. Meher NK. Cai C. Singh SK. Rev. Soc. Quim. Mex. 2004, 48: 275

Google Scholar
23a Katritzky AR. He H.-Y. Suzuki K. J. Org. Chem. 2000, 65: 8210

Crossref PubMed Google Scholar
23b Katritzky AR. Yang H. Zhang S. Wang M. ARKIVOC 2002, (xi): 39

Crossref PubMed Google Scholar
23c Katritzky AR. Rogovoy BV. Kirichenko N. Vvedensky V. Bioorg. Med. Chem. Lett. 2002, 12: 1809

Crossref PubMed Google Scholar
24 Katritzky AR. Yang H. Zhang S. Wang M. ARKIVOC 2002, (xi): 39

Google Scholar
25 Katritzky AR. Hoffmann S. Suzuki K. ARKIVOC 2004, (xii): 14

Google Scholar
26 Katritzky AR. Pastor A. Voronkov MV. J. Heterocycl. Chem. 1999, 36: 777

Crossref Google Scholar
27 Katritzky AR. Angrish P. Steroids 2006, 71: 660

Crossref Google Scholar
28 Katritzky AR. Angrish P. Synthesis 2006, 4135

Article in Thieme Connect Google Scholar
29a Katritzky AR. Suzuki K. Singh SK. He H.-Y. J. Org. Chem. 2003, 68: 5720

Crossref Google Scholar
29b Zou X. Wang X. Cheng C. Kong L. Mao H. Tetrahedron Lett. 2006, 47: 3767

Crossref Google Scholar
30a Katritzky AR. Pastor A. J. Org. Chem. 2000, 65: 3679

Crossref Google Scholar
30b Katritzky AR. Jiang R. Suzuki K. J. Org. Chem. 2005, 70: 4993

Crossref Google Scholar
30c Katritzky AR. Meher NK. Singh SK. J. Org. Chem. 2005, 70: 7792

Crossref Google Scholar
31 Katritzky AR. Abdel-Fattah AAA. Wang M. J. Org. Chem. 2003, 68: 1443

Crossref PubMed Google Scholar
32 Katritzky AR. Abdel-Fattah AAA. Wang M. J. Org. Chem. 2003, 68: 4932

Crossref Google Scholar
33 Katritzky AR. Abdel-Fattah AAA. Akhmedova RG. ARKIVOC 2005, (vi): 329

Google Scholar
34 Katritzky AR. Abdel-Fattah AAA. Gromova AV. Witek R. Steel PJ. J. Org. Chem. 2005, 70: 9211

Crossref Google Scholar
35 Katritzky AR. Suzuki K. Singh SK. Croat. Chem. Acta 2004, 77: 175

Google Scholar
36a Katritzky AR. Suzuki K. Singh SK. Synthesis 2004, 2645

Crossref Google Scholar
36b Katritzky AR. Angrish P. Hür D. Suzuki K. Synthesis 2005, 397

Crossref Google Scholar
36c Katritzky AR. Angrish P. Suzuki K. Synthesis 2006, 411

Crossref Google Scholar
36d Katritzky AR. Todadze E. Cusido J. Angrish P. Shestopalov AA. Chem. Biol. Drug Des. 2006, 68: 37

Crossref Google Scholar
36e Katritzky AR. Todadze E. Shestopalov AA. Cusido J. Angrish P. Chem. Biol. Drug Des. 2006, 68: 42

Crossref Google Scholar
36f Katritzky AR. Meher G. Angrish P. Chem. Biol. Drug Des. 2006, 68: 326

Crossref Google Scholar
36g Katritzky AR. Tao H. Jiang R. Suzuki K. Kirichenko K. J. Org. Chem. 2007, 72: 407

Crossref Google Scholar
36h Katritzky AR. Mohapatra PP. Fedoseyenko D. Duncton M. Steel PJ. J. Org. Chem. 2007, 72: 4268

Crossref Google Scholar
36i Katritzky AR. Angrish P. Narindoshvili T. Bioconjugate Chem. 2007, 18: 994

Crossref Google Scholar
36j Katritzky AR. Todadze E. Angrish P. Draghici B. J. Org. Chem. 2007, 72: 5794

Crossref Google Scholar
37 Katritzky AR. Cai C. Suzuki K. Singh SK. J. Org. Chem. 2004, 69: 811

Crossref PubMed Google Scholar
38 Katritzky AR. Singh SK. Cai C. Bobrov S. J. Org. Chem. 2006, 71: 3364

Crossref Google Scholar
39 Katritzky AR. Singh SK. Akhmedova R. Cai C. Bobrov S. ARKIVOC 2007, (vi): 6

Google Scholar
40a Katritzky AR. Le KNB. Khelashvili L. Mohapatra PP. J. Org. Chem. 2006, 71: 9861

Crossref Google Scholar
40b Wang X. Zhang Y. Tetrahedron 2003, 59: 4201

Crossref Google Scholar
40c Wang X. Zhang Y. Tetrahedron Lett. 2002, 43: 5431

Crossref Google Scholar
41 Wang X. Zou X. Li J. Hu Q. Synlett 2005, 3042

Article in Thieme Connect Google Scholar
42a Wang X. Zou X. Du J. J. Chem. Res. 2006, 64

Article in Thieme Connect Google Scholar
42b Katritzky AR. Shestopalov AA. Suzuki K. Synthesis 2004, 1806

Article in Thieme Connect Google Scholar
43 Singh KN. Kaur A. Synth. Commun. 2005, 35: 2935

Crossref Google Scholar
44a Katritzky AR. Widyan K. Kirichenko K. J. Org. Chem. 2007, 72: 5802

Google Scholar
44b Katritzky AR. Wang M. Zhang S. ARKIVOC 2001, (ix): 19

Google Scholar
45 Katritzky AR. Huang T.-B. Voronkov MV. Steel PJ. J. Org. Chem. 2000, 65: 8069

Crossref Google Scholar
46 Katritzky AR. Singh SK. Bobrov S. J. Org. Chem. 2004, 69: 9313

Crossref PubMed Google Scholar
47 Burmistrov SI. Belykh VS. Dovgalyuk NV. Zh. Khim. 1978, 7Zh228 ; Chem. Abstr. 1978, 89, 43232

Google Scholar
48 Jorand J. Oleagineux 1960, 15: 183

Google Scholar
49 Coulthard CE. Marshall J. Payman FL. J. Chem. Soc. 1930, 280

Google Scholar
50 Korshunov SP. Korzhova NV. Kazantseva VM. Krasnov VL. Utekhina NV. Bodrikov IV. Zh. Org. Khim. 1986, 22: 1847

Google Scholar