Simple and efcient synthesis of 2,2′‑arylmethylenebis(3‑hydroxy‑5,5‑dimethyl‑2‑cy…
Table 1 The synthesis of 2,2′-arylmethylenebis(3-hydroxy-5,5-dime-
thyl-2-cyclohexene-1-one) derivatives in the presence of MS-4A
All products are known compounds and have satisfactory
melting points and spectral data (1H NMR) which are identi-
cal with those reported in the literature [12, 16, 29].
Acknowledgements Open access funding provided by Budapest Uni-
versity of Technology and Economics (BME). Á. M. is grateful to
the József Varga Foundation for the fnancial support. The research
reported in this paper has been supported by the National Research,
Development and Innovation Fund (TUDFO/51757/2019-ITM, The-
matic Excellence Program).
Entry
R
Product Yielda/% M.p./°C/Lit. m.p./°C
credit to the original author(s) and the source, provide a link to the
Creative Commons license, and indicate if changes were made.
1
2
3
4
5
6
7
8
9
C6H5
3a
3b
3c
3d
3e
3f
90
98
98
97
99
96
97
99
97
98
3-BrC6H4
4-BrC6H4
4-ClC6H4
4-CH3C6H4
4-OCH3C6H4
3-NO2C6H4
4-NO2C6H4
References
3g
3h
1. Song G, Wang B, Luo H, Yang L (2007) Catal Commun 8:673
2. Jin T-S, Zhang J-S, Xiao J-C, Wang A-Q, Li T-S (2004) Synlett
5:366
4-(CH3)2NC6H4 3i
CH3(CH2)2 3j
10
3. Jin T-S, Zhang J-S, Wang A-Q, Li T-S (2005) Synth Commun
35:2339
Reaction conditions: 2 mmol dimedone, 1 mmol aldehyde, 0.1 g
MS-4A, 3 cm3 EtOH, refux, 5 h
4. Saha M, Dey J, Ismail K, Pal AK (2011) Lett Org Chem 8:554
5. Shanmugasundaram P, Prabahar KJ, Ramakrishnan VT (1993) J
Heterocycl Chem 30:1003
aIsolated yield
6. Srividya N, Ramamurthy P, Shanmugasundaram P, Ramakrishnan
VT (1996) J Org Chem 61:5083
under mild conditions. The desired products were formed
with excellent yields (90–99%). The catalyst is a commer-
cially available and cheap material, which is widely used as a
drying agent in synthetic laboratories. It can be easily recov-
ered from the reaction mixture and reused several times.
7. Josephrajan T, Ramakrishnan VT, Kathiravan G, Muthumary J
(2005) Arkivoc 11:124
8. Josephrajan T, Ramakrishnan VT (2007) Can J Chem 85:572
9. Maharvi GM, Ali S, Riaz N, Afza N, Malik A, Ashraf M, Iqbal
L, Lateef M (2008) J Enzyme Inhib Med Chem 23:62
10. Ali S, Maharvi GM, Riaz N, Afza N, Malik A, Rehman AU,
Lateef M, Iqbal L (2009) West Indian Med J 58:92
11. Khan KM, Maharvi GM, Khan MTH, Shaikh AJ, Perveen S,
Begum S, Choudhary MI (2006) Bioorg Med Chem 14:344
12. Zhang Y, Shang Z (2010) Chin J Chem 28:1184
13. Vaid R, Gupta M, Kant R, Gupta VK (2016) J Chem Sci 128:967
14. Saha M, Pal AK, Nandi S (2012) RSC Adv 2:6397
15. Rahmani S, Zeynizadeh B (2019) Res Chem Int 45:1227
16. Li J-T, Li Y-W, Song Y-L, Chen G-F (2012) Ultrason Sonochem 19:1
17. Gupta M, Gupta M (2016) J Chem Sci 128:849
18. Gilanizadeh M, Zeynizadeh B (2018) New J Chem 42:8553
19. Rao VK, Kumar MM, Kumar A (2011) Indian J Chem 50B:1128
20. Magyar Á, Hell Z (2019) Catal Lett 149:2528
21. Magyar Á, Hell Z (2019) Synlett 30:89
Experimental
1H NMR spectra were obtained on BRUKER Avance-500
instrument using TMS as an internal standard in CDCl3. Melt-
ing points were determined on Gallenkamp apparatus. All com-
pounds and solvents were purchased from Merck Hungary, Ltd.
General procedure for the preparation of 2,2′‑aryl‑
methylenebis(3‑hydroxy‑5,5‑dimethyl‑2‑cyclo‑
hexene‑1‑one) derivatives
22. Magyar Á, Nagy B, Hell Z (2015) Catal Lett 145:1876
23. Magyar Á, Hell Z (2016) Catal Lett 146:1153
24. Magyar Á, Hell Z (2017) Period Polytech Chem Eng 61:278
25. Magyar Á, Hell Z (2018) Green Proc Synth 7:316
26. Magyar Á, Hell Z (2016) Monatsh Chem 147:1583
27. Han X, Ma C, Wu Z, Huang G (2016) Synthesis 48:351
28. Esmaeili AA, Ghalandarabad SA, Zangouei M (2012) Tetrahedron
Lett 53:5605
A typical reaction was carried out in a 10 cm3 fask. Dime-
done (2 mmol), aldehyde (1 mmol), 0.1 g MS-4A, and
3 cm3 ethanol were stirred at refux temperature for 5 h. The
catalyst was heated at 120 °C for 1 h before the reaction to
remove the traces of water. The progression of the reac-
tion was monitored by TLC. After completion, the solid was
fltered and washed with ethanol and then the fltrate was
29. Ramachary DB, Kishor M (2007) J Org Chem 72:5056
Publisher’s Note Springer Nature remains neutral with regard to
jurisdictional claims in published maps and institutional afliations.
1
evaporated. The product was subjected to H NMR spec-
troscopy and its melting point was measured.
1 3