Vitamin B1 as a metal-ion-free natural catalyst for sustainable quinoxaline ring condensation
623
Tavares GA, Vangrevelinghe E, Blasco F, Ottaviani G, Ossola F,
Scesa J, Reetz J (2010) Bioorg Med Chem Lett 20:2609
20. Ramalingam P, Ganapaty S, Babu Rao C (2010) Bioorg Med
Chem Lett 20:406
General procedure for preparation of quinoxalines
under ultrasound irradiation
All reactions were carried out in an open vessel which was
kept at 25 °C using a temperature-controlled water bath.
The temperature inside the reactor was monitored using a
Precision Temperature Logger EBI-2T Type 311 (pos-
sessing an external probe) from ebroÒ Electronic GmbH &
Co KG. The recorded temperature within 1 h was
36–37 °C.
A mixture of benzene-1,2-diamine (1.1 mmol), 1,2-
diketone (1 mmol), and crystalline VB1 (5 mol%) was
taken in 5 cm3 methanol and sonicated for the appropriate
reaction time (Table 3). After completion of the reaction
[monitored by TLC using ethyl acetate/hexane (3:7 v/v) or
GC], the organic medium was removed with a rotary
evaporator under reduced pressure. Water (10 cm3) was
added to the resulting solid mixture and filtered to afford
the product 1. The crude products were purified by flash
chromatography to afford pure products for analytical
measurements.
21. Tanimori S, Nishimura T, Kirihata M (2009) Bioorg Med Chem
Lett 19:4119
22. Ajani OO, Obafemi CA, Ikpo CO, Ogunniran KO, Nwinyi OC
(2009) Chem Heterocycl Compd 45:1370
23. Weng Q, Wang D, Guo P, Fang L, Hu Y, He Q, Yang B (2008)
Eur J Pharmacol 581:262
´
24. Villar R, Vicente E, Solano B, Perez-Silanes S, Aldana I, Maddry
JA, Lenaerts AJ, Franzblau SG, Cho S-H, Monge A, Goldman
RC (2008) J Antimicrob Chemother 62:547
25. Carta A, Piras S, Loriga G, Paglietti G (2006) Mini-Rev Med
Chem 6:1179
26. Hassan SY, Khattab SN, Bekhit AA, Amer A (2006) Bioorg Med
Chem Lett 16:1753
27. Perumal RV, Mahesh R (2006) Bioorg Med Chem Lett 16:2769
28. Jaso A, Zarranz B, Aldana I, Monge A (2005) J Med Chem
48:2019
29. Brown DJ (2004) Quinoxalines: Supplement II. In: Taylor EC,
Wipf P (eds) The chemistry of heterocyclic compounds. Wiley,
New Jersey
30. Huang T-K, Wang R, Shi L, Lu X-X (2008) Catal Commun
9:1143
31. Srinivas C, Kumar CNSSP, Jayathirtha Rao V, Palaniappan S
(2007) J Mol Catal A Chem 265:227
32. Heravi MM, Bakhtiari K, Tehrani MH, Javadi NM, Oskooie HA
(2006) Arkivoc xvi:16
33. Heravi MM, Tehrani MH, Bakhtiari K, Oskooie HA (2007) Catal
Commun 8:1341
References
1. Jordan F, Patel MS (eds) (2004) Thiamine: catalytic mechanisms
in normal and disease states. Marcel Dekker, New York
2. Breslow R (1958) J Am Chem Soc 80:3719
3. Sheenan JC, Hara T (1974) J Org Chem 39:1196
4. Shinkai S, Yamashita T, Kusano Y, Manabe O (1980) Tetrahe-
dron Lett 21:2543
34. Kumar A, Kumar S, Saxena A, De A, Mozumdar S (2008) Catal
Commun 9:778
35. Ajaikumar S, Pandurangan A (2009) Appl Catal A Gen 357:184
36. More SV, Sastry MNV, Yao C-F (2006) Green Chem 8:91
37. More SV, Sastry MNV, Wang C-C, Yao C-F (2005) Tetrahedron
Lett 46:6345
5. Kluger R (1987) Chem Rev 87:863
38. Bhosale RS, Sarda SR, Ardhapure SS, Jadhav WN, Bhusare SR,
Pawar RP (2005) Tetrahedron Lett 46:7183
39. Cai JJ, Zou JP, Pan XQ, Zhang W (2008) Tetrahedron Lett
49:7386
6. Scheffold R, Abrecht S, Orlinski R, Ruf H-R, Stamouli P,
Tinembart O, Walder L, Weymuth C (1987) Pure Appl Chem
59:363
7. Du¨nkelmann P, Jung DK, Nitsche A, Demir AS, Siegert P, Lin-
gen B, Baumann M, Pohl M, Mu¨ller M (2002) J Am Chem Soc
124:12084
8. Malandrinos G, Louloudi M, Hadjiliadis N (2006) Chem Soc Rev
35:684
9. Mikolajek R, Spiess AC, Bu¨chs J (2007) J Biotech 129:723
10. Stamatis A, Malandrinos G, Butler IS, Hadjiliadis N, Louloudi M
(2007) J Mol Catal A Chem 267:120
11. Noonan C, Baragwanath L, Connon SJ (2008) Tetrahedron Lett
49:4003
40. Mason TJ (1997) Chem Soc Rev 26:443
41. Cintas P, Luche J-L (1999) Green Chem 1:115
42. Mason TJ (2007) Ultrason Sonochem 14:476
43. Mason TJ (2003) Ultrason Sonochem 10:175
44. Mason TJ, Cintas P (2002) In: Clark J, Macquarrie D (eds)
Handbook of green chemistry and technology. Blackwell
Science, Oxford, p 372
45. Aghapoor K, Darabi HR, Mohsenzadeh F, Balavar Y, Daneshyar
H (2010) Transit Metal Chem 35:49
46. Darabi HR, Aghapoor K, Mohsenzadeh F, Taala F, As-
adollahnejad N, Badiei A (2009) Catal Lett 133:84
47. Darabi HR, Tahoori F, Aghapoor K, Taala F, Mohsenzadeh F
(2008) J Braz Chem Soc 19:1646
12. Kluger R, Tittmann K (2008) Chem Rev 108:1797
13. Pimpim RS, Rubega CCC, de Bravo RVF, Kascheres C (1997)
Synth Commun 27:811
14. Bag S, Vaze VV, Degani MS (2006) J Chem Res 267
15. Goswami S, Hazra A (2009) Chem Lett 38:484
16. Lei M, Ma L, Hu L (2009) Tetrahedron Lett 50:6393
17. Mandhane PG, Joshi RS, Nagargoje DR, Gill CH (2010) Tetra-
hedron Lett 51:3138
18. Urleb U (1998) In: Schaumann E (ed) Methods of organic
chemistry (Houben-Weyl), Vol. E9b/Part 2 (Hetarenes IV). Thi-
eme, Stuttgart, p 193
48. Darabi HR, Mohandessi S, Aghapoor K, Mohsenzadeh F (2007)
Catal Commun 8:389
49. Mohsenzadeh F, Aghapoor K, Darabi HR (2007) J Braz Chem
Soc 18:297
50. Aghapoor K, Darabi HR, Mohsenzadeh F (2005) Z Naturforsch
60b:901
51. Chakraborti AK, Bhagat S, Rudrawar S (2004) Tetrahedron Lett
45:7641
19. Pissot-Soldermann C, Gerspacher M, Furet P, Gaul C, Holzer P,
McCarthy C, Radimerski T, Regnier CH, Baffert F, Drueckes P,
52. Sithambaram S, Ding Y, Li W, Shen X, Gaenzlera F, Suib SL
(2008) Green Chem 10:1029
123