A facile solvent-free one-pot three-component method for the synthesis of 2-amino-4H-pyrans and tetrahydro-4H-chromenes at ambient temperature

Monatshefte fur Chemie

Volumn 144, Issue 8, 2013, Pages 1219-1225

  Amirnejad, Meysam ^a   Naimi Jamal, Mohammad Reza ^a   Tourani, Hesam ^a   Ghafuri, Hossein ^a  

^a IRAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Iran)

Author keywords

2 Amino 4H pyrans; Ball milling; Multi component reactions (MCRs); One pot synthesis; Solvent free; Tetrahydro 4H chromenes

Indexed keywords

EID: 84880789586     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-013-0938-2     Document Type: Article

References (54)

1. Sheldon RA (1996) J Mol Catal A 107:75
2. Horváth IT, Anastas PT (2007) Chem Rev 107:2169
3. Kaupp G (2003) CrystEngComm 5:117
4. Kaupp G (2006) CrystEngComm 8:794
5. Naimi-Jamal MR, Mashkouri S, Sharifi A (2010) Mol Divers 14:473
6. Mashkouri S, Naimi-Jamal MR (2009) Molecules 14:474
7. Kaupp G, Schmeyers J, Naimi-Jamal MR, Zoz H, Ren H (2002) Chem Eng Sci 57:763
8. Kaupp G, Naimi-Jamal MR, Ren H, Zoz H (2003) Process Worldwide 6:24
9. Mokhtari J, Naimi-Jamal MR, Hamzeali H, Dekamin MG, Kaupp G (2009) ChemSusChem 2:248
10. Naimi-Jamal MR, Mokhtari J, Dekamin MG, Kaupp G (2009) Eur J Org Chem 21:3567
11. Kaupp G, Naimi-Jamal MR, Stepanenko V (2003) Chem Eur J 9:4156
12. Baron A, Martinez J, Lamaty F (2010) Tetrahedron Lett 51:6246
13. Mack J, Shumba M (2007) Green Chem 9:328
14. Tullberg E, Peters D, Frejd T (2004) J Organomet Chem 689:3778
15. Kaupp G, Naimi-Jamal MR, Schmeyers J (2003) Tetrahedron 59:3753
16. Lutz W (2002) Drug Discovery Today 7(Suppl.2):143
17. Gerencsér J, Dormán G, Darvas F (2006) QSAR Comb Sci 25:439
18. Ramón DJ, Yus M (2005) Angew Chem Int Ed 44:1602
19. Green GR, Evans JM, Vong AK (1995) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive Heterocyclic Chemistry II, vol 5. Permagon Press, Oxford, p 469
20. Martínez-Grau A, Marco J (1997) Bioorg Med Chem Lett 7:3165
21. Wang JL, Liu D, Zhang ZJ, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES, Huang Z (2000) Proc Natl Acad Sci 97:7124
22. Zhang YL, Chen BZ, Zheng KQ, Xu ML, Zhang LZ, Lei XH (1982) Acta Pharm Sinica 17:17
23. Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med Chem 28:517
24. Foye WO (1991) Prinicipi di Chimica Farmaceutica. Piccin, Padova, p 416
25. Witte EC, Neubert P, Roesch A (1986) 7-(Piperazinylpropoxy)-2H-1- benzopyran-2-ones. Ger Offen DE3427985, Jan 30, 1986
26. Witte EC, Neubert P, Roesch A (1986) Chem Abstr 104:224915
27. Hafez EA, Elnagdi MH, Elagamey AA, El-Taweel FA (1987) Heterocycles 26:903
28. Armesto D, Horspool WM, Martin N, Ramos A, Seoane C (1989) J Org Chem 54:3069
29. Konkoy CS, Fick DB, Cai SX, Lan NC, Keana JFW (2000) Substituted 5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyrans and benzothiopyrans and their use as potentiators of AMPA. Patent WO 2000075123, Dec 14, 2000
30. Konkoy CS, Fick DB, Cai SX, Lan NC, Keana JFW (2000) Chem Abstr 134:29313
31. Litvinov YM, Shestopalov AM (2011) Synthesis, Structure, Chemical Reactivity, and Practical Significance of 2-Amino-4H-pyrans. In: Katritzky AR (ed) Advances in Heterocyclic Chemistry, vol 103. Academic Press, Oxford, p 175
32. Khan AT, Lal M, Ali S, Khan MM (2011) Tetrahedron Lett 52:5327
33. Gao S, Tsai CH, Tseng C, Yao C-F (2008) Tetrahedron 64:9143
34. Lu G-P, Cai C (2011) J Heterocycl Chem 48:124
35. Wang L-M, Shao J-H, Tian H, Wang Y-H, Liu B (2006) J Fluorine Chem 127:97
36. Seshu Babu N, Pasha N, Venkateswara Rao KT, Sai Prasad PS, Lingaiah N (2008) Tetrahedron Lett 49:2730
37. Hasaninejad A, Shekouhy M, Golzar N, Zare A, Doroodmand MM (2011) Appl Catal A 402:11
38. Pratap UR, Jawale DV, Netankar PD, Mane RA (2011) Tetrahedron Lett 52:5817
39. Balalaie S, Bararjanian M, Sheikh-Ahmadi M, Hekmat S, Salehi P (2007) Synth Commun 37:1097
40. Banerjee S, Horn A, Khatri H, Sereda G (2011) Tetrahedron Lett 52:1878
41. Peng Y, Song G, Huang F (2005) Monatsh Chem 136:727
42. Pore DM, Undale KA, Dongare BB, Desai UV (2009) Catal Lett 132:104
43. Heravi MM, Beheshtiha YS, Pirnia Z, Sadjadi S, Adibi M (2009) Synth Commun 39:3663
44. Lian XZ, Huang Y, Li YQ, Zheng WJ (2008) Monatsh Chem 139:129
45. Peng Y, Song G (2007) Catal Commun 8:111
46. Safaei HR, Shekouhy M, Rahmanpur S, Shirinfeshan A (2012) Green Chem 14:1696
47. Sharifi A, Mirzaei M, Naimi-Jamal MR (2006) Monatsh Chem 137:213
48. Kumar D, Reddy VB, Sharad S, Dube U, Kapur S (2009) Eur J Med Chem 44:3805
49. Wang X-S, Zeng Z-S, Zhang M-M, Li Y-L, Shi D-Q, Tu SJ, Wei X-Y, Zong Z-M (2006) J Chem Res 2006:228
50. Marco JL, de los Ríos C, García AG, Villarroya M, Carreiras MC, Martins C, Eleutério A, Morreale A, Orozco M, Luque FJ (2004) Bioorg Med Chem 12:2199
51. Elgemeie GEH, Gohar AEKM, Regaila HA, Elfahham HA (1988) Arch Pharm 321:131
52. Shestopalov AM, Niazimbetova ZI, Evans DH, Niyazymbetov ME (1999) Heterocycles 51:1101
53. Sabitha G, Arundhathi K, Sudhakar K, Sastry BS, Yadav JS (2009) Synth Commun 39:433
54. Dyachenko VD, Chernega AN (2006) Russ J Org Chem 42:567