M. Bakthadoss et al. / Tetrahedron Letters 49 (2008) 820–823
823
Acknowledgements
atti, V.; Usherwood, P. N. R.; Melchiorre, C. J. Med. Chem. 1999, 42,
212–5223.
5
1
9. Witherup, K. M.; Ransom, R. W.; Graham, A. C.; Bernad, A. M.;
Salvatore, M. J.; Lumma, W. C.; Anderson, P. S.; Pitzenberger, S. M.;
Varga, S. L. J. Am. Chem. Soc. 1995, 117, 6682–6685.
We thank DST (New Delhi) for the financial support
under the fast track scheme. We thank DST-FIST for the
funding programme at the Department of Organic Chemis-
try, University of Madras, Chennai.
20. The X-ray crystal structure data of 4f and 4l have been deposited at
the Cambridge Crystallographic Data Centre and allocated the
deposition numbers CCDC 659316 (4f), CCDC 659165 (4l).
2
1. Typical experimental procedure: Methyl 1,2,3,3a,4,9b-hexahydro-1-
methyl-3-phenylchromeno[4,3-b]pyrrole-3a-carboxytate (4a): A mix-
ture of methyl (2E)-2-(2-formylphenoxy)methyl-3-phenylacrylate (3a)
(2 mmol, 0.592 g) and sarcosine (2 mmol, 0.178 g) in acetonitrile
(8 mL) was refluxed for 5 h. After the completion of the reaction as
indicated by TLC, the reaction mixture was concentrated and the
resulting crude mass was diluted with water (15 mL) and extracted
with ethyl acetate (3 Â 15 mL). The combined organic layer was
References and notes
1
2
3
4
. Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Soc. Rev. 2007, 36,
581–1588.
. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103,
11–891.
. Basavaiah, D.; Rao, P. D.; Hyma, S. Tetrahedron 1996, 52, 8001–
062.
. Ciganek, E.. In Org. React.; Paquette, L. A., Ed.; Wiley: New York,
997; Vol. 51, pp 201–350.
1
8
8
washed with brine (2 Â 10 mL) and dried over anhydrous Na
2 4
SO .
The organic layer was concentrated and purified by column
chromatography on silica gel (Acme 100–200 mesh), using ethyl
acetate–hexanes (1:9) to afford the pure methyl 1,2,3,3a,4,9b-hexa-
hydro-1-methyl-3-phenylchromeno[4,3-b]pyrrole-3a-carboxytate (4a)
as a colourless solid in 91% yield.
1
5
6
7
8
9
. Basavaiah, D.; Aravindu, K. Org. Lett. 2007, 9, 2453–2456.
. Reiser, U.; Jauch, J. Synlett 2001, 90–92.
. Basavaiah, D.; Satyanarayana, T. Org. Lett. 2001, 3, 3619–3622.
. Padwa, A. Pure Appl. Chem. 2003, 75, 47–62. Ó 2003 IUPAC.
. Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642–2645.
Compound 4a: mp 112–114 °C; IR (KBr): 3036, 2956, 2846,
À1
1
1738 cm
; H NMR: d 2.54 (s, 3H), 2.96 (t, 1H, J = 9.9 Hz), 3.38
1
0. Paquette, L. A.; Hu, Y.; Luxenburger, A.; Bishop, R. L. J. Org.
Chem. 2000, 72, 209–222.
(dd, 1H, J = 3.0, 10.2 Hz), 3.63 (s, 1H), 3.66 (d, 1H, J = 11.0 Hz);
3.72 (s, 3H), 3.76 (dd, 1H, J = 3.0, 10.2 Hz), 4.02 (d, 1H,
J = 11.0 Hz), 6.82–6.94 (m, 2H), 7.14–7.33 (m, 7H); C NMR: d
1
3
11. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484–
4517.
39.79, 48.50, 52.04, 52.37, 60.80, 65.81, 66.99, 116.92, 119.71, 120.02,
1
1
1
1
2. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765–2809.
3. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863–909.
4. Zeng, W.; Zhou, Y. G. Tetrahedron Lett. 2007, 48, 4619–4622.
5. Basavaiah, D.; Bakthadoss, M.; Pandiaraju, S. Chem. Commun 1998,
127.21, 128.25, 128.82, 129.02, 131.38, 138.02, 154.47, 173.82. MS
+
(m/z): 324 (M +1). Anal. Calcd for C20
H
21NO
3
: C, 74.28; H, 6.55; N,
4.33. Found: C, 74.74; H, 6.33; N, 4.60.
Compound 4i: mp 102–104 °C; IR (KBr): 3033, 2920, 2850,
À1
1
1
639–1640.
6. Basavaiah, D.; Bakthadoss, M.; Jayapal Reddy, G. Synthesis 2001, 6,
19–923.
7. Basavaiah, D.; Bakthadoss, M.; Jayapal Reddy, G. Synth. Commun.
002, 35, 689–697.
2237 cm
; H NMR: d 2.58 (s, 3H), 2.88 (t, 1H, J = 9.6 Hz), 3.25
1
1
1
(dd, 1H, J = 7.5, 9.6 Hz), 3.50 (dd, 1H, J = 7.5, 9.6 Hz), 3.63 (s, 1H),
1
3
9
4.25 (s, 2H), 6.95–7.04 (m, 2H), 7.20–7.46 (m, 7H); C NMR: d 39.56,
46.03, 48.19, 61.82, 67.10, 67.70, 117.71, 118.76, 118.86, 121.29,
2
128.28, 128.85, 128.93, 129.83, 131.02, 137.47, 153.95. MS (m/z): 291
+
8. Rosini, M.; Budriesi, R.; Bixel, M. G.; Bolognesi, M. L.; Chiarini, A.;
Hucho, F.; Krogsgaard-Larsen, P.; Mellor, A.; Minarini, A.; Tumi-
(M +1). Anal. Calcd for C19
H
18
N
2
O
1
: C, 78.59; H, 6.25; N, 9.65.
Found: C, 78.30; H, 6.09; N, 9.21.