2632
J. M. Rodríguez, M. Dolors Pujol / Tetrahedron Letters 52 (2011) 2629–2632
Table 2 (continued)
Entry
Aldehyde/ketone
R
Method
A (yield %)
B (yield %)
Mp (°C) (Lit.) of A
a
b
c
––
84
<5
Trace
O
––*
Cl
CHO
––
16
17
H
122–124 (hexane/ethyl acetate)
O
CHO
a
b
81
90
––
––
H
46–48 (45–46)24
⁄⁄
Method a: microwave, 90 °C, 25 min; Method b: ultrasound, 60 °C, 45 min. Method c: microwave, 90 °C, 60 min. Starting material.
*
Side products of Michael reaction.
12. 1,4-Benzodioxan-5-carbaldehyde
was
obtained
from
the
2,3-
Acknowledgments
dihydroxybenzaldehyde by treatment with 1,2-dibromethane and K2CO3 in
DMF at 80 °C in a 92% of yield.
We are grateful to the Minister of Science and Technology
(CTQ2007-60614/BQU), for the financial support. One of us (J.R.)
thanks the Minister of Education and Science (Government of
Spain) for a fellowship.
13. Gairaud, C. B.; Lappin, G. R. J. Org. Chem. 1953, 18, 1–3.
14. (a) Dingwalla, J. G.; Ehrenfreund, J.; Hall, R. G. Tetrahedron 1989, 45, 3787–
3808; (b) Popp, B. V.; Thorman, J. L.; Morales, C. M.; Landis, C. R.; Shahl, S. S. J.
Am. Chem. Soc. 2004, 126, 14832–14842.
15. Tinsley, S. W. J. Org. Chem. 1961, 26, 4723–4724.
16. Dauksas, V.; Milvydiene, G. D. I. Mendeleeva 1966, 11, 474–475 (CAN
65:99316).
17. Dauzonne, D.; Royer, R. Chem. Pharm. Bull. 1986, 34, 1628–1633.
18. Büchi, G.; Mak, C.-P. J. Org. Chem. 1977, 42, 1784–1786.
19. Canoira, L.; Gonzalo Rodríguez, J.; Subirats, J. B.; Escario, J. A.; Jiménez, I.;
Martínez-Fernández, A. R. Eur. J. Med. Chem. 1989, 24, 39–42.
20. Dornow, A.; Boberg, F. Just. Lieb. Ann. Chem. 1952, 578, 101–112.
21. Masayuki, F. Bull. Chem. Soc. Jpn. 1988, 61, 4029–4035.
22. King, W. J.; Nord, F. F. J. Org. Chem. 1949, 14, 405–410.
References and notes
1. Perrone, M. G.; Santandrea, E.; Bleve, L.; Vitale, P.; Colabufo, N. A.; Jockers, R.;
Milazzo, F. M.; Sciarroni, A. F.; Scilimati, A. Bioorg. Med. Chem. 2008, 16, 2473–
2488.
2. Czekelius, C.; Carreira, E. M. Org. Lett. 2004, 6, 4575–4577.
3. Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452–6455.
4. Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett. 2002, 4, 2621–2623.
5. Dwivedi, A. P.; Kumar, S.; Varshney, V.; Singh, A. B.; Srivastava, A. K.; Sahu, D. P.
Bioorg. Med. Chem. Lett. 2008, 18, 2301–2305.
23. Bourguignon, J.; Le Nard, G.; Queguiner, G. Can. J. Chem. 1985, 63, 2354–
2361.
24. Gawley, R. E.; Chemburkar, S. R. Heterocycles 1989, 29, 1283–1292.
25. All compounds gave satisfactory spectroscopic and analytical data. Analytical
data given only for the new compounds: 5-(2-nitrovinyl)-2,3-dihydro-1,4-
benzodioxane. Yellow solid, mp 112–114 °C (hexane/ethyl acetate). Rf = 0.6
(hexane/ethyl acetate 5:5). NMR (CDCl3, 300 MHz) d (ppm), 4.41 (m, 2H, CH2O–);
4.42 (m, 2H, CH2O–); 6.98 (d, J = 7.5 Hz, 1H, H-8);7.02–7.04(m, 2H, H-6andH-7);
7.85 (d, J = 13.7 Hz, 1H, CH=); 8.07 (d, J = 13.7 Hz, 1H, CH@). NMR 13C (CDCl3,
50.3 MHz) d (ppm), 64,0 and 64.5 (CH2, CH2O–); 112.9 (CH, C-8); 114.7 (C, C-5);
117.0 (CH, C-6); 122.7 (CH, C-7); 132.0 (CH, CH-NO2); 137.4 (CH, CH-C-5); 145.2
(C, C-4a); 146.2 (C, C-8a). 6-Chloro-3-(1-hydroxy-2-nitroethyl)-4H-chromen-4-
one. Yellow solid, mp 122–124 °C (hexane/ethyl acetate). Rf = 0.19 (hexane/ethyl
acetate 5:5). NMR 1H (CDCl3, 300 MHz) d (ppm), 1.56 (bs, 1H, OH); 4.13 (m, 1H,
CHO–); 4.89 (d, J = 6 Hz, 1H, CH-NO2); 5.02 (d, J = 6 Hz, 1H, CH-NO2); 7.42 (d,
J = 8.5 Hz, 1H, H-8); 7.69 (d, J = 8.5 Hz, 1H, H-7); 7.97 (s, 1H, H-2); 8.16 (s, 1H, H-
5). NMR 13C (CDCl3, 50.3 MHz) d (ppm), 62.4 (CH, CHOH); 79.6 (CH2, CH2-NO2);
113.5 (C, C-8); 117.8 (C, C-3); 123.8 (C, C-4a); 127.4 (C, C-6); 132.4 (CH, C-5);
133.2 (CH, C-7); 145.2 (CH, C-2); 153.1 (C, C-8a); 182.9 (C, C@O).
6. (a) Ballini, R.; Castagnani, R.; Petrini, M. J. Org. Chem. 1992, 57, 2160–2164;
Bauer, H. H.; Urbas, L. In The Chemistry of the Nitro and Nitroso Group; Feuer, H.,
Ed.; Interscience: New York, 1970; pp 75–200. Chapter 2; (c) Ono, N. The Nitro
Group in Organic Synthesis; Wiley-VCH: New York, 2001. Chapter 3, p 30; (d)
Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon:
Oxford, 1996. Vol 2, pp 321-340; (e) Luzzio, F. A. Tetrahedron 2001, 57, 915–
945.
7. Andrew, R. G.; Raphael, R. A. Tetrahedron 1987, 43, 4803–4812.
8. (a) Varma, R. S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 5131–5134;
(b) Abdallah-El Ayoubi, S.; Texier-Boullet, F.; Hamelin, J. Synthesis 1994, 258–
260.
9. (a) Chetia, A.; Longchar, M.; Lekhok, K. C.; Boruah, R. C. Synlett 2004, 1309–
1311; (b) Gan, C.; Chen, X.; Lai, G.; Wang, Z. Synlett 2006, 387–390.
10. Mc Nulty, J.; Steere, J. A.; Wolf, S. Tetrahedron Lett. 1998, 39, 8013–8016.
11. Raner, K. D.; Strauss, C. R.; Vyskoc, F.; Mokbel, L. J. Org. Chem. 1993, 58,
950–958.