References
1a
Henry L.
Bull. Soc. Chim. Fr.
1895,
13:
999
1b
Luzzio FA.
Tetrahedron
2001,
57:
915
1c
Comprehensive Organic Synthesis
Vol. 1:
Trost BM.
Pergamon;
Oxford:
1999.
p.321
1e
Adams JP.
J. Chem. Soc., Perkin Trans. 1
2002,
2586
1f
Seebach D.
Knochel P.
Helv. Chim. Acta
1984,
67:
261
2a
Posner GH.
Crouch RD.
Tetrahedron
1990,
46:
7509
2b
Denmark SE.
Senanayake CBW.
J. Org. Chem.
1993,
58:
1853
2c
Kabalka GW.
Guindi LHM.
Tetrahedron
1990,
46:
7443
2d
Handbook of Reagents for Organic Synthesis: Reagents, Auxiliaries and Catalysts for C-C Bond Formation
Coates RM.
Denmark SE.
John Wiley & Sons;
New York:
2000.
p.542
3a
Jouglet B.
Bianco L.
Rousseau G.
Synlett
1991,
907
3b
Misumi Y.
Bulman RA.
Matsumoto W.
Heterocycles
2002,
56:
599
4
Sera A.
Takagi K.
Katayama H.
Yamada H.
J. Org. Chem.
1988,
53:
1157
5a
Trost BM.
Yeh VSC.
Angew. Chem. Int. Ed.
2002,
41:
861
5b
Ballini R.
Bosica G.
Livi D.
Palmieri A.
Maggi R.
Sartori G.
Tetrahedron Lett.
2003,
44:
2271
5c
Christensen C.
Juhl K.
Hazell RG.
Jorgensen KA.
J. Org. Chem.
2002,
67:
4875
6
Varma RS.
Dahiya R.
Kumar S.
Tetrahedron Lett.
1997,
37:
5131
7
Simoni D.
Rondanin R.
Morini M.
Baruchello R.
Invidiata FP.
Tetrahedron Lett.
2000,
41:
1607
8
Ballini R.
Bosica G.
Parrini M.
Tetrahedron Lett.
1998,
39:
7963
9a
Boger DL.
Nakahara S.
J. Org. Chem.
1991,
56:
880
9b
Comprehensive Heterocyclic Chemistry
Vol. 2:
Katrizky AR.
Rees CW.
Scrieven EFV.
Pergamon;
Oxford:
1984.
p.67
9c
Thomas D.
Ashokan CV.
Tetrahedron Lett.
2002,
43:
2273
9d
Shintani T.
Kadono H.
Kikuchi T.
Schubert T.
Shogase Y.
Shimazaki M.
Tetrahedron Lett.
2003,
44:
6567
9e
Kobayashi K.
Yoneda K.
Mizumoto T.
Umakoshi H.
Morikawa O.
Konishi H.
Tetrahedron Lett.
2003,
44:
4733
9f
Li H.
Petersen JL.
Wang KK.
J. Org. Chem.
2003,
68:
5512
9g
Du W.
Curren DP.
Org. Lett.
2003,
5:
1765
9h
Bagley MC.
Date JW.
Bower J.
Synlett
2001,
1149
10a
Boruah RC.
Ahmed S.
Sharma U.
Sandhu JS.
J. Org. Chem.
2000,
65:
922
10b
Sharma U.
Ahmed S.
Boruah RC.
Tetrahedron Lett.
2000,
41:
3493
10c
Boruah RC.
Ahmed S.
Sharma U.
Sandhu JS.
Indian J. Chem.: Sect. B
1999,
38:
274
10d
Ahmed S.
Boruah RC.
Tetrahedron Lett.
1996,
37:
8251
11a
Varma RS.
Reactions under Solvent Free ‘Dry’ Condition in Microwaves: Theory and Application in Material Processing IV
Clark DE.
Sutton WH.
Lewis DA.
American Ceramic Society, Ceramic Transactions, Westerville;
OH:
1997.
p.357
11b
Varma RS.
Dahiya R.
Tetrahedron
1998,
54:
6293
11c
Ranu BC.
Hajra A.
Jana U.
Tetrahedron Lett.
2000,
41:
531
11d
Bose AK.
Manhas MS.
Sharma AK.
Banik BK.
Synthesis
2002,
1578
11e
Perreux L.
Loupy A.
Tetrahedron
2001,
57:
9199
11f
Lidstrom P.
Tierney J.
Wathey B.
Westman J.
Tetrahedron
2001,
57:
9225
11g
Bora U.
Saikia A.
Boruah RC.
Org. Lett.
2003,
5:
435
12 All compounds gave satisfactory spectroscopic and analytical data. Spectral data of representative compound 10: Yield: 90%; mp 208-209 °C; Rf = 0.5 (toluene-EtOAc, 95:5). IR (KBr): 2938, 1730, 1521, 1373 cm-1. 1H NMR (CDCl3): δ = 8.02 (s, 1 H), 5.24 (br s, 1 H), 4.56 (br s, 1 H), 2.50 (s, 3 H), 2.20 (s, 3 H), 1.10 (s, 3 H), 1.09 (s, 3 H), 2.34-1.06 (m, 17 H). 13C NMR (CDCl3): δ = 177.2, 173.3, 170.5, 140.3, 135.2, 134.4, 128.6, 121.7, 73.7, 55.9, 55.5, 50.4, 38.1, 36.8, 33.3, 31.3, 30.7, 29.9, 28.9, 21.4, 20.5, 19.3, 17.2, 17.0, 14.5. MS (ESI): m/z = 447.53 [M+ + 23]. Anal. Calcd for C25H32O4N2: C, 70.73; H, 7.59; N, 6.51. Found: C, 71.26; H, 7.86; N, 6.05. Compound 14: Yield: 86%; mp 78-79 °C; Rf = 0.55 (toluene-EtOAc, 95:5). IR (KBr): 2945, 1525, 1360 cm-1. 1H NMR (CDCl3): δ = 8.05 (s, 1 H), 3.60-3.25 (m, 4 H), 2.05 (s, 3 H), 2.00-1.78 (m, 4 H). 13C NMR (CDCl3): δ = 169.5, 168.7, 140.5, 137.2, 136.5, 55.1, 54.8, 50.3, 47.6, 16.4. MS (ESI): m/z = 215.74 [M+ + 23]. Anal. Calcd for C10H12O2N2: C, 62.49; H, 6.29; N, 14.57. Found: C, 62.30; H, 6.56; N, 14.35.
13
Urrutia A.
Rodriguez JG.
Tetrahedron Lett.
1998,
39:
4143
14a
Corey EJ.
Estreicher H.
J. Am. Chem. Soc.
1978,
100:
6294
14b
Barrett AGM.
Chem. Soc. Rev.
1991,
20:
95