Synthesis 2016; 48(21): 3684-3695
DOI: 10.1055/s-0035-1562519
short review
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Synthesis of Heterocycles with α-Haloketones as the Key Building Blocks

Veronika Fülöpová
a   Department of Organic Chemistry, Faculty of Science, Palacký University, 771 46 Olomouc, Czech Republic
,
Miroslav Soural*
a   Department of Organic Chemistry, Faculty of Science, Palacký University, 771 46 Olomouc, Czech Republic
b   Institute of Molecular and Translation Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00, Olomouc, Czech Republic   Email: e-mail_soural@orgchem.upol.cz
› Author Affiliations
Further Information

Publication History

Received: 31 May 2016

Accepted after revision: 18 June 2016

Publication Date:
11 August 2016 (online)


Abstract

This short review summarizes the use of α-haloketones in the preparation of various heterocycles with the application of solid-phase synthesis. A literature survey revealed that eighteen different five-to-seven membered scaffolds are accessible, including condensed heterocycles and bisheterocycles.

1 Introduction

2 Thiazoles: Path A

3 Thiazolo[2,3-b]quinazolines: Path A

4 Dihydroimidazo[2,1-b]thiazoles: Path A

5 Imidazo[1,2-a]pyrimidines: Path A

6 Benzodiazepinones: Path A

7 Benzothiadiazepine 1,1-Dioxides: Path A/B

8 Benzothiazine 1,1-Dioxides: Path B

9 Morpholines: Path B

10 Imidazoles: Path B

11 Thiophenes: Path A

12 Thiophenes: Path B

13 Pyridazinones: Path A

14 Pyrroles: Path A

15 Pyrroles: Path B

16 Piperazines: Path A

17 Oxazoles: Path B

18 Quinolines: Path B

19 Indazoles: Path C

20 Quinazolines: Path C

21 Indoles: Path C

22 Conclusion

 
  • References

    • 1a Bouillon I, Zajíček J, Pudelová N, Krchňák V. J. Org. Chem. 2008; 73: 9027
    • 1b Schütznerová E, Krchňák V. ACS Comb. Sci. 2015; 17: 137
  • 2 Merrifield RB. J. Am. Chem. Soc. 1963; 85: 2149
  • 3 Hlaváč J, Soural M, Krchňák V. Practical Aspects of Combinatorial Solid-Phase Synthesis. In Solid-Phase Organic Synthesis: Concepts, Strategies, and Applications. Toy PH, Lam Y. John Wiley & Sons; Hoboken: 2012: 95
  • 4 Pons JF, Mishir Q, Nouvet A, Brookfield F. Tetrahedron Lett. 2000; 41: 4965
  • 5 Kazzouli SE, Berteina-Raboin S, Mouaddib A, Guillaumet G. Tetrahedron Lett. 2002; 43: 3193
  • 6 Stadlwieser J, Ellmerer-Müller EP, Takó A, Maslouh N, Bannwarth W. Angew. Chem. Int. Ed. 1998; 37: 1402
  • 7 Soural M, Bouillon I, Krchňák V. J. Comb. Chem. 2008; 10: 923
  • 8 Dadiboyena S, Nefzi A. Synthesis 2012; 44: 215
  • 9 Murru S, Nefzi A. ACS Comb. Sci. 2014; 16: 39
  • 10 Sreejalekshmi KG, Devi SK. C, Rajasekharan KN. Tetrahedron Lett. 2006; 47: 6179
  • 11 Cohrt AE, Nielsen TE. ACS Comb. Sci. 2014; 16: 71
  • 12 Li Y, Giulianotti M, Houghten RA. Tetrahedron Lett. 2010; 51: 5637
  • 13 Bouillon I, Krchňák V. J. Comb. Chem. 2007; 9: 912
  • 14 Li Y, Giulianotti M, Houghten RA. Tetrahedron Lett. 2011; 52: 696
  • 15 Chen Y, Lam Y, Lai YH. Org. Lett. 2002; 4: 3935
  • 16 Kazzouli SE, Berteina-Raboin S, Mouaddib A, Guillaumet G. Tetrahedron Lett. 2003; 44: 6265
  • 17 Kamal A, Devaiah V, Reddy KL, Rajesh R, Shetti RV. C. R, Shankaraiah N. J. Comb. Chem. 2007; 9: 267
  • 18 Fülöpová V, Soural M. ACS Comb. Sci. 2015; 17: 570
  • 19 Fülöpová V, Gucký T, Grepl M, Soural M. ACS Comb. Sci. 2012; 14: 651
  • 20 Fülöpová V, Krchňák V. ACS Comb. Sci. 2014; 16: 412
  • 21 Fülöpová V, Krchňáková A, Schütznerová E, Zajíček J, Krchňák V. J. Org. Chem. 2015; 80: 1795
  • 22 Pudelová N, Krchňák V. J. Comb. Chem. 2009; 11: 851
  • 23 Zaragoza F. Tetrahedron Lett. 1996; 37: 6213
  • 24 Lee S, Lee D, Song KS, Liu KH, Gong YD, Lee T. Tetrahedron 2014; 70: 9183
  • 25 Huang X, Tang J. Tetrahedron 2003; 59: 4851
  • 26 Tang J, Huang X. J. Chem. Res. 2003; 599
  • 27 Trautwein AW, Süssmuth RD, Jung G. Bioorg. Med. Chem. Lett. 1998; 8: 2381
  • 28 Vaňková B, Brulíková L, Wu B, Krchňák V. Eur. J. Org. Chem. 2012; 5075
  • 29 Pulici M, Quartieri F, Felder ER. J. Comb. Chem. 2005; 7: 463
  • 30 Soural M, Hradil P, Křupková S, Hlaváč J. Mini. Rev. Org. Chem. 2012; 9: 426
  • 31 Soural M, Krchňák V. J. Comb. Chem. 2007; 9: 793
    • 32a Soural M, Hlaváč J, Funk P, Džubák P, Hajdúch M. ACS Comb. Sci. 2010; 13: 39
    • 32b Kadrić J, Motyka K, Džubák P, Hajdúch M, Soural M. Tetrahedron Lett. 2014; 55: 3592
    • 32c Křupková S, Soural M, Hlaváč J, Hradil P. J. Comb. Chem. 2009; 11: 951
  • 33 Vaňková B, Hlaváč J, Soural M. J. Comb. Chem. 2010; 12: 890
  • 34 Bouillon I, Zajíček J, Pudelová N, Krchňák V. J. Org. Chem. 2008; 73: 9027
    • 35a Pudelová N, Krchňák V. J. Comb. Chem. 2009; 11: 370
    • 35b Kočí J, Krchňák V. J. Comb. Chem. 2010; 12: 168
    • 36a Křupková S, Slough GA, Krchňák V. J. Org. Chem. 2010; 75: 4562
    • 36b Fülöpová V, Cziesla L, Fleming M, Lu Y, Voelker A, Krchňák V. ACS Comb. Sci. 2015; 17: 470