Solid-supported sulfonic acid-containing catalysts efficiently promoted one-pot multi-component synthesis of β-acetamido carbonyl compounds

Journal of Chemical Sciences

Volumn 124, Issue 2, 2012, Pages 501-508

  Zolfigol, Mohammad Ali ^a   Khazaei, Ardeshir ^a   Zare, Abdolkarim ^b   Mokhlesi, Mohammad ^a   Hekmat Zadeh, Tahereh ^b   Hasaninejad, Alireza ^c   Derakhshan Panah, Fatemeh ^a   Moosavi Zare, Ahmad Reza ^a   Keypour, Hassan ^a   Dehghani Firouzabadi, Ahmad Ali ^d   Merajoddin, Maria ^b  

^a BU ALI SINA UNIVERSITY   (Iran)

^b PAYAME NOOR UNIVERSITY   (Iran)

^c PERSIAN GULF UNIVERSITY   (Iran)

^d YAZD UNIVERSITY   (Iran)

Author keywords

acetamido ester; acetamido ketone; enolizable ketone; silica functionalized sulfonic acid (SFSA); Solid supported catalysts; sulfuric acid modified polyethylene glycol 6000 (PEG OSO3H)

Indexed keywords

ACETAMIDO; ACETAMIDO ESTERS; ACETOACETATES; ACETYL CHLORIDE; COMPLEX STRUCTURE; ESTER DERIVATIVES; MULTICOMPONENT CONDENSATION; MULTICOMPONENTS; ONE POT; SHORT REACTION TIME; SULFONIC ACID; SULFURIC ACID-MODIFIED POLYETHYLENE GLYCOL-6000 (PEG-OSO3H);

ACETONITRILE; CHLORINE COMPOUNDS; ESTERIFICATION; ESTERS; KETONES; POLYETHYLENE GLYCOLS; SILICA;

SULFURIC ACID;

EID: 84863192872     PISSN: 09743626     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-011-0210-4     Document Type: Article

References (41)

1. Domling A and Ugi I 2000 Angew Chem. Int. Ed. 39 3169
2. Vijaynair C R, Vinod A U, Bindu S, Sreekanth A R and Lakshmibalagopal J S 2003 Acc. Chem Res. 36 899
3. Zhu J and Bienayme H Multicomponent Reactions, Weinheim, Germany, Wiley-VCH, 2005
4. Hasaninejad A, Zare A, Shekouhy M and Ameri Rad J 2010 J. Comb. Chem. 12 844-849
5. Zolfigol M A, Khazaei A, Moosavi-Zare A R, Zare A and Khakyzadeh V 2011 Appl. Catal. A: General 400 70-81
6. Khazaei A, Zolfigol M A, Moosavi-Zare A R, Zare A, Parhami A and Khalafi-Nezhad A 2010 Appl. Catal. A: General 386 179-187
7. K Kobinata M Uramoto M Nishii H Kusakabe G Nakamura K Isono 1980 Agric. Biol. Chem. 44 1709 10.1271/bbb1961.44.1709 1:CAS:528:DyaL3cXlvFygur0%3D
8. M Mukhopadhyay B Bhatia J Iqbal 1997 Tetrahedron Lett 38 1038 10.1016/S0040-4039(96)02474-4
9. H Mao J Wan Y Pan 2009 Tetrahedron 65 1026 10.1016/j.tet.2008.11.071 1:CAS:528:DC%2BD1cXhsFajtrbP
10. J Barluenga AL Viado E Aguilar S Fustero 1993 J. Org. Chem. 58 5972 10.1021/jo00074a024 1:CAS:528:DyaK3sXmt1Kgtb0%3D
11. D Bahulayan SK Das J Iqbal 2003 J. Org. Chem. 68 5735 5738 10.1021/jo020734p 1:CAS:528:DC%2BD3sXktlGqsL4%3D
12. EN Prbhakaran J Iqbal 1999 J. Org. Chem. 64 3339 3341 10.1021/jo981239p
13. MM Heravi L Ranjbar F Derikvand FF Bamoharram 2007 J. Mole. Catal. A: Chemical 276 266
14. L Nagarapu R Bantu R Puttireddy 2007 Appl. Catal. A: General 332 304 10.1016/j.apcata.2007.08.033 1:CAS:528:DC%2BD2sXht1ShtrrF
15. VS Shinu B Sheej E Purushothaman D Bahulayan 2009 Tetrahedron Lett. 50 4838 10.1016/j.tetlet.2009.06.022 1:CAS:528:DC%2BD1MXosVGku7Y%3D
16. AR Momeni M Sadeghi 2009 Appl. Catal. A: General 357 100 10.1016/j.apcata.2009.01.019 1:CAS:528:DC%2BD1MXitFKmsLY%3D
17. AK Tiwari RM Kumbhare SB Agawane AZ Ali KV Kumar 2008 Bioorg. Med. Chem. Lett. 18 4130 4132 10.1016/j.bmcl.2008.05.088 1:CAS:528:DC%2BD1cXoslequ7c%3D
18. MT Maghsoodlou A Hassankhani HR Shaterian SM Habibi-Khorasani E Mosaddegh 2007 Tetrahedron Lett. 48 1729 10.1016/j.tetlet.2007.01.060 1:CAS:528:DC%2BD2sXhsFyrsbc%3D
19. R Ghosh S Maiti A Chakraborty S Chakraborty AK Mukherjee 2006 Tetrahedron 62 4059 10.1016/j.tet.2006.02.037 1:CAS:528:DC%2BD28XjslCgsro%3D
20. L Nagarapu S Kantevari VN Cheemalapati S Apuri NV Kumari 2007 J. Mol. Catal. A: Chemical 264 22 25 10.1016/j.molcata.2006.09.001 1:CAS:528: DC%2BD2sXit12ltLs%3D
21. AT Khan LH Choudhury T Parvin M Asif Ali 2006 Tetrahedron Lett. 47 8137 10.1016/j.tetlet.2006.09.041 1:CAS:528:DC%2BD28XhtVyksLzJ
22. B Das M Krishnaiah K Laxminarayana KR Reddy 2007 J. Mole. Catal. A: Chemical 270 284 10.1016/j.molcata.2007.02.014 1:CAS:528:DC%2BD2sXkslyjt7o%3D
23. Clark J H and Rhodes C N Clean synthesis using porous inorganic solid catalysts and supported reagents, 1st ed., UK: Royal Society of Chemistry, 2000
24. Salehi P, Zolfigol M A, Shirini F and Baghbanzadeh M 2006 Curr. Org. Chem. 10 2171 (Review)
25. Khalafi-Nezhad A, Parhami A, Bargebid R, Molazade S, Zare A and Foroughi H 2011 Mol. Divers. 15 373-381
26. Zare A, Hasaninejad A, Shekouhy M and Moosavi Zare A R 2008 Org. Prep. Proced. Int. 40 457
27. Shimizu K, Hayashi E, Hatamachi Y, Kodama T and Kitayama Y 2004 Tetrahedron Lett. 45 5135
28. Karimi B and Khalkhali M 2007 J. Mol. Catal. A: Chemical 271 75
29. Das B, Kanth B S, Reddy K R and Kumar A S 2008 J. Heterocycl Chem. 45 1499
30. Gupta R, Paul S and Loupy A 2006 J. Mol. Catal. A: Chemical 266 50
31. Das B, Suneel K, Venkateswarlu K and Ravikanth B 2008 Chem. Pharm. Bull. 56 366
32. Das B, Venkateswarlu K, Holla H and Krishnaiah M 2006 J. Mol. Catal. A: Chemical 253 107
33. Das B, Venkateswarlu K, Krishnaiah M and Holla H 2006 Tetrahedron Lett. 47 8693
34. Ciardelli F, Tsuchida E, Wohrle D 1996, Springer Verlag: Berlin, Heidelberg Macromolecule-metal complexes
35. Wang L, Han J, Tian H, Sheng J, Fan Z and Tang X 2005 Synlett 337
36. Wang X, Quan Z, Wang F, Wang M, Zhang Z and Li Z 2006 Synth. Commun. 36 451
37. Hasaninejad A, Zare A and Shekouhy M 2011 Tetrahedron 67 390
38. Kiasat A R and Mehrjardi M F 2008 Catal. Commun. 9 1497
39. Zare A, Hasaninejad A, Rostami E, Moosavi-Zare A R and Merajoddin M 2010 Trans. C. Chemistry and Chemical Eng. 17 24
40. Zare A, Hasaninejad A, Shekouhy M, Saleh Hoseini Ghattali S M and Golzar N 2011 J. Iran. Chem. Soc. 8 411
41. Hasaninejad A, Zare A, Shekouhy M and Ameri-Rad J 2011 Green Chem. 958.