Citation: Mohammad Piltan. One-pot synthesis of pyrrolo[1,2-a]quinoxaline and pyrrolo[1,2-a]pyrazine derivatives via the three-component reaction of 1,2-diamines, ethyl pyruvate and a-bromo ketones[J]. Chinese Chemical Letters, ;2014, 25(11): 1507-1510. doi: 10.1016/j.cclet.2014.06.013 shu

One-pot synthesis of pyrrolo[1,2-a]quinoxaline and pyrrolo[1,2-a]pyrazine derivatives via the three-component reaction of 1,2-diamines, ethyl pyruvate and a-bromo ketones

Mohammad Piltan ^,

1.
Department of Chemistry, Sanandaj Branch, Islamic Azad University, P.O. Box 618, Sanandaj, Iran

Corresponding author: Mohammad Piltan,
Received Date: 19 February 2014
Available Online: 30 May 2014

A simple synthetic protocol has been developed involving the three-component reaction between 1,2-diamines, ethyl pyruvate and α-bromo ketones in the presence of FeCl₃ as a catalyst. A number of pyrrolo[1,2-a]quinoxaline and pyrrolo[1,2-a]pyrazine derivatives were synthesized in excellent yields using this protocol.
- Pyrrolo[1,2-a]quinoxaline,
- α-Bromo ketones,
- 1,2-Diamines,
- Ethyl pyruvate
1. [1]
  [1] L. Weber, Multi-component reactions and evolutionary chemistry, Drug Discov. Today 7 (2002) 143-147.
2. [2]
  [2] G. Balme, E. Bossharth, N. Monteiro, Pd-assisted multicomponent synthesis of heterocycles, Eur. J. Org. Chem. 21 (2003) 4101-4111.
3. [3]
  [3] J. Zhu, H. Bienaymé , Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
4. [4]
  [4] R.A. Smits, H.D. Lim, A. Hanzer, et al., Fragment based design of new H4 receptor- ligands with anti-inflammatory properties in vivo, J. Med. Chem. 51 (2008) 2457- 2467.
5. [5]
  [5] A. Furlan, F. Colombo, A. Kover, et al., Identification of new aminoacid amides containing the imidazo[2,1-b]benzothiazol-2-ylphenyl moiety as inhibitors of tumorigenesis by oncogenic Met signaling, Eur. J. Med. Chem. 47 (2012) 239-254.
6. [6]
  [6] R. David, Changing therapeutic paradigms in glaucoma management, Exp. Opin. Invest. Drug 7 (1998) 1063-1086.
7. [7]
  [7] F. Colombo, C. Tintori, A. Furlan, et al., ‘Click' synthesis of a triazole-based inhibitor of Met functions in cancer cells, Bioorg. Med. Chem. Lett. 22 (2012) 4693-4696.
8. [8]
  [8] M.A. Naylor, M.A. Stephen, J. Nolan, et al., Heterocyclic mono-N-oxides with potential applications as bioreductive anti-tumour drugs: Part 1. 8-Alkylamino- substitued phenylimidazo[1,2-a]quinoxalines, Anticancer Drug Res. 8 (1993) 439-461.
9. [9]
  [9] C.S. Yi, S.Y. Yun, Scope and mechanistic study of the ruthenium-catalyzed ortho- C-H bond activation and cyclization reactions of arylamines with terminal alkynes, J. Am. Chem. Soc. 127 (2005) 17000-17006.
10. [10]
  [10] R. Abonia, B. Insuasty, J. Quiroga, H. Kolshorn, H. Meier, A versatile synthesis of 4,5-dihydropyrrolo[1,2-a]quinoxalines, J. Heterocycl. Chem. 38 (2001) 671-674.
11. [11]
  [11] N.T. Patil, R.D. Kavthe, V.S. Raut, V.V.N. Reddy, Platinum-catalyzed formal Markownikoff's hydroamination/hydroarylation cascade of terminal alkynes assisted by tethered hydroxyl groups, J. Org. Chem. 74 (2009) 6315-6318.
12. [12]
  [12] N.T. Patil, P.G.V.V. Lakshmi, V. Singh, Au(I)-catalyzed direct hydroamination- hydroarylation and double hydroamination reactions of terminal alkynes, Eur. J. Org. Chem. 24 (2010) 4719-4731.
13. [13]
  [13] A. Correa, O.G. Mancheno, C. Bolm, Iron-catalyzed carbon-heteroatom and heteroatom-heteroatom bond forming processes, Chem. Soc. Rev. 37 (2008) 1108-1117.
14. [14]
  [14] M. Piltan, L. Moradi, S.A. Zarei, H. Rostami, One-pot multicomponent synthesis of novel tricyclic pyrrolo[2,1-c][1,4]benzoxazines, Chin. Chem. Lett. 25 (2014) 234-236.
15. [15]
  [15] I. Yavari, M. Piltan, L. Moradi, Synthesis of pyrrolo[2,1-a]isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline, Tetrahedron 65 (2009) 2067-2071.
16. [16]
  [16] M. Piltan, L. Moradi, G. Abasi, S.A. Zarei, A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate, Beilstein J. Org. Chem. 9 (2013) 510-515.
17. [17]
  [17] L. Moradi, M. Piltan, H. Rostami, G. Abasi, One-pot synthesis of pyrrolo[1,2-a]pyrazines via three component reaction of ethylenediamine, acetylenic esters and nitrostyrene derivatives, Chin. Chem. Lett. 24 (2013) 740-742.
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