1
058
V. B. Labade et al.
Fig. 1 Proposed mechanism for
CsF catalyzed Aza-Michael
addition
CsF
N
H
F
Cs
X
N
H
N
X
F Cs
H
N
CsF
X
temperature for the appropriate time (see Table 2). Pro-
gress of the reaction was monitored using TLC. Upon
completion, the reaction mixture was extracted with ethyl
10. Cardillo G, Tomasini C (1996) Chem Soc Rev 25:117
1
1. Hagiwara E, Fujii A, Sodeoka M (1998) J Am Chem Soc
20:2474
2. Adrian JC, Snapper ML (2003) J Org Chem 68:2143
1
1
3
acetate (10 cm 92), and the organic layer was dried over
13. Ambhaikar NB, Snyder JP, Liotta DC (2003) J Am Chem Soc
125:3690
anhydrous sodium sulfate. Ethyl acetate was distilled under
reduced pressure to afford the desired compound. Obtained
materials were identical to the compounds described in
1
1
1
4. Jenner G (1995) Tetrahedron Lett 36:233
5. Loh TP, Wei LL (1998) Synlett 9:975
6. Bartoli G, Bosco M, Marcantoni E, Petrini M, Sambri L, Tor-
regiani E (2001) J Org Chem 66:9052
[
26].
1
1
1
2
7. Srivastava N, Banik BK (2003) J Org Chem 68:2109
8. Varala R, Alam MM, Adapa SR (2003) Synlett 5:720
9. Wabnitz TC, Spencer JB (2002) Tetrahedron Lett 43:3891
0. Xu LW, Li L, Xia CG (2004) Helv Chim Acta 87:1522
Ultrasound method
Corresponding amine 1 (1 mmol) and a,b-unsaturated
compound 2 (1.1 mmol) were added to a 25-cm conical
3
flask containing 10 cm water, and to this 10 mol% of CsF
3
21. Azizi N, Saidi MR (2004) Tetrahedron 60:383
22. Shaikh NS, Deshpande VH, Bedekar AV (2001) Tetrahedron
5
7:9045
was added. The reaction mixture was irradiated in an
ultrasonicator for 20–40 min (Table 2). The progress of the
reaction was monitored using TLC. Upon completion, the
2
3. Yadav JS, Reddy BVS, Basak AK, Narsaiah AV (2003) Chem
Lett 32:988
24. Xu LW, Li JW, Zhou SL, Xia CG (2004) New J Chem 28:183
25. Kantam ML, Neeraja V, Kavita B, Neelima B, Chaudhari MK,
Hussain S (2005) Adv Synth Catal 347:763
3
reaction mixture was extracted with ethyl acetate (10 cm
9
2) and the organic layer was dried over anhydrous
2
6. Pawar SS, Dekhane DV, Thore SN, Shingare MS (2008) J Het-
erocycl Chem 45:1869
sodium sulfate. Ethyl acetate was distilled under reduced
pressure to afford the desired compounds. The obtained
materials were identical to the compounds described in
27. Xiang C, Jin S, Zhicai S, Jun W, Peizhi Z (2008) Synthesis
24:3931
2
8. Lowe H, Hessel V, L o¨ b P, Hubbard S (2006) Org Processs Res
Dev 10:1144
[
26].
2
3
9. Breslow R (2004) Acc Chem Res 37:471
0. Mason TJ, Lorimer JP (1988) Sonochemistry: Theory,
Application and Uses of Ultrasound in Chemistry. Wiley,
New York
1. Gaplovsky A, Gaplovsky M, Toma S, Luche JL (2000) J Org
Chem 65:8444
2. Deshmukh RR, Rajagopal R, Srinivasan KV (2001) Chem
Commun 17:1544
3. Cravotto G, Cintas P (2006) Chem Soc Rev 35:180
Acknowledgments The authors would like to thank Professor C.
H. Gill, Head of the Department of Chemistry, and Dr. Babasaheb
Ambedkar, Marathwada University, Aurangabad, for providing the
necessary facilities.
3
3
3
References
1
2
3
. Perlmutter P (1992) Conjugate addition reaction in organic syn-
thesis. Pergamon Press, Oxford
. Lee VJ (1991) In: Comprehensive Organic Synthesis. Trost BM,
Fleming I (eds), Pergamon Press, New York
. Bull SD, Davies SG, Delgado-Ballester S, Fenton G, Kelly PM,
Smith AD (2000) Synlett 1257
. Christoffers J (1998) Eur J Org Chem 7:1259
. Giuseppone N, Van de Weghe P, Fellah M, Collin J (1998)
Tetrahedron 54:13129
34. Richards W, Loomis A (1927) J Am Chem Soc 49:3086
35. Greenwood NN, Earnshaw A (1984) Chemistry of the elements.
Pergamon Press, Oxford
36. Fiorenza M, Mordini A, Papaleo S, Pastorelli S, Ricci A (1985)
Tetrahedron Lett 26:787
37. Lee JC, Choi Y (1998) Synth Commun 28:2021
38. Singh RP, Kirchmeier RL, Shreeve JM (1999) Org Lett 1:1047
39. Khan KM, Hayat S, Zia-Ullah Atta-ur-Rahman, Choudhary MI,
Maharvi GM, Bayer E (2003) Synth Commun 33:3435
40. Shah STA, Khan KM, Hussain H, Anwar MU, Fecker M, Voelter
W (2005) Tetrahedron 61:6652
4
5
6
. Hagiwara H, Okamoto T, Harada N, Uda H (1995) Tetrahedron
5
1:9891
. Enders D, Wahl H, Bettray W (1995) Angew Chem Int Ed 34:455
. Simpkins NS (1990) Tetrahedron 46:6951
7
8
9
41. Shah STA, Khan KM, Hussain H, Hayat S, Voelter W (2005)
Monatsh Chem 136:1583
42. Chancharunee S, Pinhom P, Pohmakotr M, Perlmutter P (2009)
Synth Commun 38:880
. Durst T (1979) In: Comprehensive Organic Chemistry. Barton
DHR, Oills WD (eds), Pergamon Press, Oxford
1
23