Thermal and Microwave-Assisted
Rapid Syntheses of Substituted Imidazo[1,2-a]pyridines Under Solvent- and
Catalyst-Free Conditions

Kaushik C. Chunavala; Girdhar Joshi; Eringathodi Suresh; Subbarayappa Adimurthy

doi:10.1055/s-0030-1258405

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Synthesis 2011(4): 635-641
DOI: 10.1055/s-0030-1258405

PAPER

Thermal and Microwave-Assisted Rapid Syntheses of Substituted Imidazo[1,2-a]pyridines Under Solvent- and Catalyst-Free Conditions

Kaushik C. Chunavala, Girdhar Joshi, Eringathodi Suresh, Subbarayappa Adimurthy*
Central Salt and Marine Chemicals Research Institute (CSIR), G. B. Marg, Bhavnagar 364 002, Gujarat, India
Fax: +91(278)2567562; e-Mail: sadimurthy@yahoo.com;

Further Information

Publication History

Received 15 November 2010
Publication Date:
12 January 2011 (online)

Abstract
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Abstract

Thermal and microwave-assisted rapid syntheses of highly substituted imidazo[1,2-a]pyridine derivatives by reaction of aminopyridines and α-bromo-β-keto esters under solvent-free conditions are described. Reactions carried out under microwave irradiation give the highest yields of products in reaction times of less than two minutes.

Key words

aminopyridines - α-bromo-β-keto esters - imidazo[1,2-a]pyridines - microwave irradiation - solvent-free - thermal

References

1 For a general review on the chemistry of imidazopyridine derivatives, see: Couty F. Evano G. In Comprehensive Heterocyclic Chemistry III Vol. 2: Katritzky AR. Ramsden CA. Scriven EFV. Taylor RJK. Elsevier; Oxford: 2008. p.409-499

Google Scholar
2a Guillaumet G, Berteina-Raboin S, El Kazzouli S, Delagrange P, and Caignard DH. inventors; WO2006027474. ; Chem. Abstr. 2006, 144, 254132
2b Song G. Zhang Y. Li X. Organometallics 2008, 27: 1936

Google Scholar
2c Enguehard C. Fauvelle F. Debouzy J. Peinnequin A. Thery I. Dabouis V. Gueiffier A. Eur. J. Pharm. Sci. 2005, 24: 219

Google Scholar
2d Gudmundsson KS. John BA. Org. Lett. 2003, 5: 1369

Google Scholar
2e Hamdouchi C. Zhong B. Mendoza J. Collins E. Jaramillo C. Diego J. Robertson D. Spencer CD. Anderson BD. Watkins SA. Zhang F. Brooks HB. Bioorg. Med. Chem. Lett. 2005, 15: 1943

Google Scholar
3a Elhakmoui A. Gueiffier A. Milhavet JC. Blache Y. Chapat PJ. Bioorg. Med. Chem. Lett. 1994, 4: 1937

Google Scholar
3b Gueiffier A. Lhassani M. Elhakmoui A. Snoeck R. Andrei G. Chavignion O. Teulade JC. Kerbal A. Essassi M. Debouzy JC. Witurowo JP. Blache Y. Balzarini J. De Clercq E. Chapat JP. J. Med. Chem. 1996, 39: 2856

Google Scholar
3c Lhassani M. Chavignion O. Chezal JM. Teulade JC. Chapat JP. Snoeck R. Andrei G. Balzarini J. De Clercq E. Gueiffier A. J. Med. Chem. 1999, 34: 271

Google Scholar
3d Gudmundsson KS. Drach JC. Townsend LB. J. Org. Chem. 1997, 62: 3453

Google Scholar
3e Pan S. Wang G. Shinazi RF. Zhao K. Tetrahedron Lett. 1998, 39: 2695

Google Scholar
3f Hamdouchi C. de Blas J. del Prado M. Gruber J. Heinz BA. Vance L. J. Med. Chem. 1999, 42: 50

Google Scholar
3g Gudmundsson KS. Williams JD. Drach JC. Townsend LB. J. Med. Chem. 2003, 46: 1449

Google Scholar
4a Kaminski JJ. Doweyko AM. J. Med. Chem. 1999, 40: 427

Google Scholar
4b Kaminski JJ. Puchalski C. Solomon DM. Rizvi RK. Conn DJ. Elliot AJ. Lovey RG. Guzik H. Chui PJS. Long JF. McPhail AT. J. Med. Chem. 1989, 32: 1686

Google Scholar
5a Rival Y. Grassy G. Michael G. J. Med. Chem. 1992, 40: 1170

Google Scholar
5b Rewankar GR. Matthews JR. Robins RK. J. Med. Chem. 1975, 18: 1253

Google Scholar
5c Ismail MA. Arafa RK. Wenzler T. Brun R. Tanious FA. Wilson WD. Boykin DW. Bioorg. Med. Chem. 2008, 16: 683

Google Scholar
5d Odell LR. Nilsson MT. Gising J. Lagerlund O. Muthas D. Nordqvist A. Karlen A. Larhed M. Bioorg. Med. Chem. Lett. 2009, 19: 4790

Google Scholar
6a Beswick PJ, Campbell IB, and Naylor A. inventors; WO9631509. ; Chem. Abstr. 1997, 126, 8117j
6b Abignente E. Acta Chim. Therap. 1991, 18: 1253

Google Scholar
6c Gudmundsson KS. Johns BA. Bioorg. Med. Chem. Lett. 2007, 17: 2735

Google Scholar
7a Tully WR. Gardner CR. Gillespie RJ. Westwood R. J. Med. Chem. 1991, 34: 2060

Google Scholar
7b Trapani G. Franco M. Latrofa A. Ricciardi L. Carotti A. Serra M. Sanna E. Biggio G. Liso G. J. Med. Chem. 1999, 42: 3934

Google Scholar
7c Trapani G. Franco M. Ricciardi L. Latrofa A. Genchi G. Sanna E. Tuveri F. Gagetti E. Biggio G. Liso G. J. Med. Chem. 1997, 40: 3109

Google Scholar
8 Sanfilippo PJ. Urbanski M. Press JB. Dubinsky B. Moore JB. J. Med. Chem. 1991, 34: 2060

Crossref Google Scholar
9 Fuchs K, Romig M, Mendla K, Briem H, and Fechteler K. inventors; WO0214313. ; Chem. Abstr. 2002, 136, 183824r
10 Zhuang Z.-P. Kung M.-P. Wilson A. Lee W.-C. Plössl K. Hou C. Holtzman DM. Kung HF. J. Med. Chem. 2003, 46: 237

Crossref PubMed Google Scholar
11a Abe Y. Kayakiri H. Satoh S. Inoue T. Sawada Y. Imai KH. J. Med. Chem. 1998, 41: 564

Google Scholar
11b Holm KJ. Goa KL. Drugs 2000, 59: 865

Google Scholar
12a El Kazzouli S. Berteina-Raboin S. Mouaddib A. Guillaumet G. Tetrahedron Lett. 2003, 44: 6265

Google Scholar
12b El Kazzouli S. Berthaut A. Berteina-Raboin S. Mouaddib A. Guillaumet G. Lett. Org. Chem. 2005, 2: 184

Google Scholar
12c Koubachi J. El Kazzouli S. Berteina-Raboin S. Mouaddib A. Guillaumet G. J. Org. Chem. 2007, 72: 7650

Google Scholar
12d Kamal A. Devaiah V. Reddy KL. Rajendar R. Shetti V. Shankaraiah N. J. Comb. Chem. 2007, 9: 267

Google Scholar
12e Herath A. Dahl R. Cosford NDP. Org. Lett. 2010, 12: 412

Google Scholar
12f Patel HS. Linn JA. Drewry DH. Hillesheim DA. Zuercher WJ. Hokstra WJ. Tetrahedron Lett. 2003, 44: 4077

Google Scholar
12g Montgomery JA. Secrist JA. In Comprehensive Heterocyclic Chemistry Vol. 5: Katritzky AR. Rees CW. Potts KT. Pergamon; Oxford: 1984. p.607

Google Scholar
13a Chernyak N. Gevorgyan V. Angew. Chem. Int. Ed. 2010, 49: 2743

Google Scholar
13b Bakherad M. Nasr-Isfahani H. Keivanloo A. Doostmohammadi N. Tetrahedron Lett. 2008, 49: 3819

Google Scholar
13c Bakherad M. Nasr-Isfahani H. Keivanloo A. Sang G. Tetrahedron Lett. 2008, 49: 6188

Google Scholar
14a Davey DD. J. Org. Chem. 1987, 52: 1863

Google Scholar
14b Galons H. Bergerat I. Farnoux CC. Miocque M. Synthesis 1982, 1103

Google Scholar
14c Knolker HJ. Boese R. Hitzemann R. Chem. Ber. 1990, 123: 327

Google Scholar
14d Liu P. Fang L. Lei X. Lin G. Tetrahedron Lett. 2010, 51: 4605

Google Scholar
14e Andaloussi M. Moreau E. Chavignon O. Teulade JC. Tetrahedron Lett. 2007, 48: 8392

Google Scholar
14f Yadav JS. Subba Reddy BV. Rao YG. Srinivas M. Narsaiah AV. Tetrahedron Lett. 2007, 48: 7717

Google Scholar
14g Adib M. Sheibani E. Zhu L.-G. Mirzaei P. Tetrahedron Lett. 2008, 49: 5108

Google Scholar
14h Kercher T. Rao C. Bencsik JR. Josey JA. J. Comb. Chem. 2007, 9: 1177

Google Scholar
14i Varma RS. Kumar D. Tetrahedron Lett. 1999, 40: 7665

Google Scholar
14j Katagiri N. Kato T. J. Heterocycl. Chem. 1984, 21: 407

Google Scholar
14k Kondo T. Kotachi S. Ogino S. Watanabe Y. Chem. Lett. 1993, 1317

Google Scholar
15a Varma RS. Pure Appl. Chem. 2001, 73: 193

Google Scholar
15b Bora U. Saikia A. Boruah RC. Org. Lett. 2003, 5: 435

Google Scholar
15c Vega JA. Vaquero JJ. Builla JA. Ezquerra J. Hamdouchi C. Tetrahedron 1999, 55: 2317

Google Scholar
15d Dimauro EF. Kennedy JM. J. Org. Chem. 2007, 72: 1013

Google Scholar
16 Adimurthy S. Malakar CC. Beifuss U. J. Org. Chem. 2009, 74: 5648

Crossref Google Scholar
18a Byth FK. Culshaw JD. Green S. Oakes SE. Thomas AP. Bioorg. Med. Chem. 2004, 14: 2245

Google Scholar
18b Katritzky AR. Xu YJ. Tu H. J. Org. Chem. 2002, 68: 4935

Google Scholar
18c Kiselyov AS. Tetrahedron Lett. 2006, 47: 2941

Google Scholar

17

X-ray crystal data for 5g: empirical formula: C₁₇H₁₆N₂O₂, formula weight: 280.32, T = 293(2) K, λ = 0.71073, crystal system: monoclinic, space group: P21/c, unit cell dimensions: a = 11.419(3) Å, b = 14.292(4) Å, c = 9.001(2) Å, β = 99.912(4)˚, V = 1447.1(6) Å^³, Z = 4, density (calcd) = 1.287 mg/m^³, absorption coefficient: 0.086 mm^-¹, F(000) = 592, crystal size: 0.32 × 0.21 × 12 mm, reflections collected: 7540, independent reflections: 2813, R ₍ _int) = 0.0225, data/restraints/parameters: 2813/0/193, goodness-of-fit on F ^² = 1.151, final R indices [I ≥ 2σ(I)], R1 = 0.0623, wR2 = 0.1392, R indices (all data): R1 = 0.0742, wR2 = 0.1456, largest diff. peak and hole: 0.204 and -0.219 eÅ^-³. CCDC 793451 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.