3-(Dichloroacetyl)chromone;
A New Building Block for the Synthesis of Formylated Purine Isosteres:
Design and Synthesis of Fused α-(Formyl)pyridines

Viktor O. Iaroshenko; Satenik Mkrtchyan; Gagik Ghazaryan; Ani Hakobyan; Aneela Maalik; Linda Supe; Alexander Villinger; Andrei Tolmachev; Dmytro Ostrovskyi; Vyacheslav Ya. Sosnovskikh; Tariel V. Ghochikyan; Peter Langer

doi:10.1055/s-0030-1258364

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 2011(3): 469-479
DOI: 10.1055/s-0030-1258364

PAPER

3-(Dichloroacetyl)chromone; A New Building Block for the Synthesis of Formylated Purine Isosteres: Design and Synthesis of Fused α-(Formyl)pyridines

Viktor O. Iaroshenko*^a,b, Satenik Mkrtchyan^a, Gagik Ghazaryan^a,c, Ani Hakobyan^a,c, Aneela Maalik^a, Linda Supe^a, Alexander Villinger^a, Andrei Tolmachev^b,d, Dmytro Ostrovskyi^a, Vyacheslav Ya. Sosnovskikh^e, Tariel V. Ghochikyan^c, Peter Langer*^a,f
^a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: viktor.iaroshenko@uni-rostock.de; e-Mail: iva108@googlemail.com;
^b National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
^c Faculty of Chemistry, Yerevan State University, Alex Manoogian 1, 0025 Yerevan, Armenia
^d Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
^e Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
^f Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

Further Information

Publication History

Received 21 October 2010
Publication Date:
15 December 2010 (online)

Abstract
Full Text
References

Buy Article Permissions and Reprints All articles of this category

Abstract

The first synthesis of 3-(dichloroacetyl)chromone from 3-(dimethylamino)-1-(2-hydroxyphenyl)propen-1-one and dichloroacetyl chloride is described. The reaction of electron-rich aminoheterocycles with 3-(dichloroacetyl)chromone provides a set of diverse fused pyridines bearing the CHCl₂-substituent at the α-position of the pyridine core. Subsequent hydrolysis leads to the formation of annulated α-(formyl)pyridines.

Key words

3-(dichloroacetyl)chromone - 4H-1-benzopyran-4-one - heterocyclic amines - fused pyridines - annulation reactions

References

1a Evans BE. Rittle KE. Bock MG. DiPardo RM. Freidinger RM. Whitter WL. Lundell GF. Veber DF. Anderson PS. Chang RSL. Lotti VJ. Cerino DJ. Chen TB. Kling PJ. Kunkel KA. Springer JP. Hirshfield J. J. Med. Chem. 1988, 31: 2235

Search in Google Scholar
1b Duarte CD. Barreiro EJ. Fraga CA. Mini-Rev. Med. Chem. 2007, 7: 1108

Search in Google Scholar
1c DeSimone RW. Currie KS. Mitchell SA. Darrow JW. Pippin DA. Comb. Chem. High Throughput Screening 2004, 7: 473

Search in Google Scholar
1d Costantino L. Barlocco D. Curr. Med. Chem. 2006, 13: 65

Search in Google Scholar
2a Dubey PK. Kumar RV. Naidu A. Kulkarni SMA. Asian J. Chem. 2002, 14: 1129

Search in Google Scholar
2b Lee SC, Choi JS, Oh JH, Park B, Kim YE, Lee JH, Shin D, Kim CM, Hyun Y.-L, Lee CS, Cho J.-M, and Ro S. inventors; WO 2007,083,978. ; Chem. Abstr. 2007, 147, 817587
2c Kelly MG, Kincaid J, Duncton M, Sahasrabudhe K, Janagani S, Upasani RB, Wu G, Fang Y, and Wei Z. L. inventors; US 2006,194,801. ; Chem. Abstr. 2006, 145, 889269
2d Randolph JT, Chen H, Degoey DA, Flentge CA, Flosi WJ, Grampovnik DJ, Huang PP, Hutchinson DK, Kempf DJ, Klein LL, and Yeung MC. inventors; US 2005,159,469. ; Chem. Abstr. 2005, 143, 641882
2e Kivlighn SD. Zingaro GJ. Gabel RA. Broten TP. Schorn TW. Schaffer LW. Naylor EM. Chakravarty PK. Patchett AA. Am. J. Hypertens. 1995, 8: 58

Search in Google Scholar
3 Stasch JP. Becker EM. Alonso-Alija C. Apeler H. Dembowsky K. Feurer A. Gerzer R. Minuth T. Perzborn E. Pleiss U. Schroder H. Schroeder W. Stahl E. Steinke W. Straub A. Schramm M. Nature 2001, 410: 212

Crossref Search in Google Scholar
4 Witherington J. Bordas V. Gaiba A. Garton NS. Naylor A. Rawlings AD. Slingsby BP. Smith DG. Takle AK. Ward RW. Bioorg. Med. Chem. Lett. 2003, 13: 3055

Crossref Search in Google Scholar
5 Mantovanini M, Melillo G, and Daffonchio L. inventors; WO 9,504,742. ; Chem. Abstr. 1995, 122, 314537
6a Tsushima M, and Kano I. inventors; EP 0,605,836. ; Chem. Abstr. 1995, 122, 31198
6b Sunagava M, Yamaga H, and Sumita I. inventors; WO 9,958,536. ; Chem. Abstr. 1999, 131, 336878
6c Kiyoaki K, Tamako T, Hiroko O, Naoki Y, Fumiya H, Yasukakatsu Y, Fukio K, Motohiro N, Tomoya M, Seiji S, Tacashi T, and Shigeharu I. inventors; US 5,200,407. ; Chem. Abstr. 1991, 114, 228904
6d Walczyński K. Zuiderveld OP. Timmerman H. Eur. J. Med. Chem. 2005, 40: 15

Search in Google Scholar
7a Connolly CJC. Hamby JM. Schroeder MC. Barvian M. Lu GH. Panek RL. Bioorg. Med. Chem. Lett. 1997, 7: 2415

Search in Google Scholar
7b Thompson AM. Delaney AM. Hamby JM. Schroeder MC. Spoon TA. Crean SM. Showalter HDH. Denny WA. J. Med. Chem. 2005, 48: 4628

Search in Google Scholar
8a Grand EK. Chase AJ. Heath C. Rahemtulla A. Cross NCP. Leukemia 2004, 18: 962

Search in Google Scholar
8b Trudel S. Ely S. Farooqi Y. Affer M. Robbiani DF. Chesi M. Bergsagel PL. Blood 2004, 103: 3521

Search in Google Scholar
9 Hedstrom L. Chem. Rev. 2009, 109: 2903

Crossref Search in Google Scholar
10a Cristalli G. Costanzi S. Lambertucci C. Lupidi G. Vittori S. Volpini R. Camaioni E. Med. Res. Rev. 2001, 21: 105

Search in Google Scholar
10b Maydanovych O. Beal PA. Chem. Rev. 2006, 106: 3397

Search in Google Scholar
10c Nair V. IMPDH Inhibitors: Discovery of Antiviral Agents against Emerging Diseases, In Antiviral Drug Discovery for Emerging Diseases and Bioterrorism Threats Torrence PF. John Wiley & Sons; Hoboken: 2005. Chap. 8. p.179-202
10d Shu Q. Nair V. Med. Res. Rev. 2008, 219
10e Agarwal RP. Pharmacol. Ther. 1982, 17: 399

Search in Google Scholar
10f Weber G. Cancer Res. 1983, 43: 3466

Search in Google Scholar
10g Inosine Monophosphate Dehydrogenase, ACS Symposium Series 839 Pankiewicz KW. Goldstein BM. American Chemical Society; Washington DC: 2003.
10h Burns CM. Chu H. Rueter SM. Hutchinson LK. Canton H. Sanders-Bush E. Emeson RB. Nature 1997, 387: 303

Search in Google Scholar
10i Higuchi M. Single FN. Kohler M. Sommer B. Sprengel R. Seeburg PH. Cell 1993, 75: 1361

Search in Google Scholar
11 Effenberger F. Maier R. Schoenwaelder KH. Ziegler T. Chem. Ber. 1982, 115: 2766

Crossref Search in Google Scholar
12a Iaroshenko VO. Volochnyuk DM. Kryvokhyzha NV. Martyloga A. Sevenard DV. Groth U. Brand J. Chernega AN. Shivanyuk AN. Tolmachev AA. Synthesis 2008, 2337
12b Iaroshenko VO. Wang Y. Sevenard DV. Volochnyuk DM. Synthesis 2009, 1851
14a Ghosh CK. J. Heterocycl. Chem. 1983, 20: 1437

Search in Google Scholar
14b Sabitha G. Aldrichim. Acta 1996, 29: 15

Search in Google Scholar
14c Ghosh CK. Heterocycles 2004, 63: 2875

Search in Google Scholar
14d Gašparová R. Lácová M. Molecules 2005, 10: 937

Search in Google Scholar
15 Ghosh CK. Pal C. Bhattacharyya A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985, 24: 914

Search in Google Scholar
16a Sosnovskikh VYa. Irgashev RA. Kodess MI. Tetrahedron 2008, 64: 2997

Search in Google Scholar
16b Sosnovskikh VYa. Khalymbadzha IA. Irgashev RA. Slepukhin PA. Tetrahedron 2008, 64: 10172

Search in Google Scholar
16c Kotljarov A. Irgashev RA. Iaroshenko VO. Sevenard DV. Sosnovskikh VYa. Synthesis 2009, 3233
16d Kotljarov A. Iaroshenko VO. Volochnyuk DM. Irgashev RA. Sosnovskikh VYa. Synthesis 2009, 3869
17 Mkrtchyan S. Iaroshenko VO. Dudkin S. Gevorgyan A. Vilches-Herrera M. Ghazaryan G. Volochnyuk D. Ostrovskyi D. Ahmed Z. Villinger A. Sosnovskikh VYa. Langer P. Org. Biomol. Chem. 2010, 8: 5280

Crossref PubMed Search in Google Scholar
18a Sosnovskikh VYa. Moshkin VS. Kodess MI. Tetrahedron Lett. 2008, 49: 6856

Search in Google Scholar
18b Sosnovskikh VYa. Moshkin VS. Kodess MI. Tetrahedron Lett. 2009, 50: 6515

Search in Google Scholar
18c Sosnovskikh VYa. Moshkin VS. Kodess MI. J. Heterocycl. Chem. 2010, 47: 629

Search in Google Scholar
18d Sosnovskikh VYa. Moshkin VS. Kodess MI. Izv. Akad. Nauk, Ser. Khim. 2010, 602 ; Russ. Chem. Bull. 2010, 59, N3
19 Ostrovskyi D. Iaroshenko VO. Petrosyan A. Dudkin S. Ali I. Villinger A. Tolmachev A. Langer P. Synlett 2010, 2299

Thieme Connect
20a Misra RN. Rawlins DB. Xiao H. Shan W. Bursuker I. Kellar KA. Mulheron JG. Sack JS. Tokarski JS. Kimball SD. Webster KR. Bioorg. Med. Chem. Lett. 2003, 13: 1133

Search in Google Scholar
20b Lin R. Connolly PJ. Lu Y. Chiu G. Li S. Yu Y. Huang S. Li X. Emanuel SL. Middleton SA. Gruninger RH. Adams M. Fuentes-Pesquera AR. Greenberger LM. Bioorg. Med. Chem. Lett. 2007, 17: 4297

Search in Google Scholar
20c Witherington J. Bordas V. Gaiba A. Garton NS. Naylor A. Rawlings AD. Slingsby BP. Smith DG. Takle AK. Ward RW. Bioorg. Med. Chem. Lett. 2003, 13: 3055

Search in Google Scholar
20d Dias LRS. Santos MB. de Albuquerque S. Castro HC. de Souza AMT. Freitas ACC. DiVaio MAV. Cabral LM. Rodriguese CR. Bioorg. Med. Chem. 2007, 15: 211

Search in Google Scholar
20e de Mello H. Echevarria A. Bernardino AM. Canto-Cavalheiro M. Leon LL. J. Med. Chem. 2004, 47: 5427

Search in Google Scholar
20f Bharate SB. Mahajan TR. Gole YR. Nambiar M. Matan TT. Kulkarni-Almeida A. Balachandran S. Junjappa H. Balakrishnan A. Vishwakarma RA. Bioorg. Med. Chem. 2008, 16: 7167

Search in Google Scholar
21a Iaroshenko VO. Sevenard DV. Kotljarov AV. Volochnyuk DM. Tolmachev AA. Sosnovskikh VYa. Synthesis 2009, 731
21b Iaroshenko VO. Wang Y. Zhang B. Volochnyuk DM. Sosnovskikh VYa. Synthesis 2009, 2393
22 Iaroshenko VO. Mkrtchyan S. Volochnyuk DM. Langer P. Sosnovskikh VYa. Ostrovskyi D. Dudkin S. Kotljarov AV. Miliutina M. Savych I. Tolmachev AA. Synthesis 2010, 2749

Thieme Connect
23 Dyson P. Hammick DL. J. Chem. Soc. 1939, 781

Crossref
24 Rubina KI. Iovel’ IG. Gol’dberg YuS. Shimanskaya MV. Chem. Heterocycl. Compd. (Engl. Transl.) 1990, 26: 43

Search in Google Scholar
25 Rubina KI. Gol’dberg YuS. Shimanskaya MV. Chem. Heterocycl. Compd. (Engl. Transl.) 1985, 21: 957

Crossref Search in Google Scholar
26a Rubina KI. Iovel’ IG. Gol’dberg YuS. Shimanskaya MV. Chem. Heterocycl. Compd. (Engl. Transl.) 1989, 24: 454

Search in Google Scholar
26b Brown BR. Hammick DL. Thewlis BH. J. Chem. Soc. 1951, 1145
27a Gammill RB. Synthesis 1979, 901
27b Yokoe I. Maruyama K. Sugita Y. Harashida T. Shirataki Y. Chem. Pharm. Bull. 1994, 42: 1697

Search in Google Scholar
28 Bodwell GJ. Hawco KM. Satou T. Synlett 2003, 879

13

Crystallographic data (excluding structure factors) for the structure 15a, 16, 23b, and 24g, reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. 801470 for 15a, 801471 for 16, 801472 for 23b, and 801473 for 24g, can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk, or via www.ccdc.cam.ac.uk/data_request/cif.