One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating

Tetrahedron

Volumn 62, Issue 19, 2006, Pages 4635-4642

  Feng, Gaofeng ^a   Wu, Jinlong ^a   Dai, Wei Min ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

1,4 Benzoxazines; 2 Aminophenols; Annulation; Microwave; Regioselectivity

Indexed keywords

2 AMINOPHENOL; 2 ETHYL 3,4 DIHYDRO 4 (2' FURYLMETHYL) 3 OXO 2H 1,4 BENZOXAZINE; 2 ETHYL 3,4 DIHYDRO 4 (2' FURYLMETHYL) 6 NITRO 3 OXO 2H 1,4 BENZOXAZINE; 2 ETHYL 3,4 DIHYDRO 4 (2' FURYLMETHYL) 7 METHYL 3 OXO 2H 1,4 BENZOXAZINE; 2 ETHYL 6,7,8,9 TETRAHYDRO 4 (2' FURYLMETHYL) 3 OXO 2H NAPHTHO[2,3 B][1,4]OXAZINE; 3,4 DIHYDRO 4 (2' FURYLMETHYL) 2 METHYL 6 NITRO 3 OXO 2H 1,4 BENZOXAZINE; 3,4 DIHYDRO 4 (2' FURYLMETHYL) 2,7 DIMETHYL 3 OXO 2H 1,4 BENZOXAZINE; 3,4 DIHYDRO 4 (2' FURYLMETHYL) 3 OXO 2 PROPYL 2H 1,4 BENZOXAZINE; 3,4 DIHYDRO 4 (2' FURYLMETHYL) 3 OXO 2H 1,4 BENZOXAZINE; 3,4 DIHYDRO 4 (2' FURYLMETHYL) 6 NITRO 3 OXO 2 PROPYL 2H 1,4 BENZOXAZINE; 3,4 DIHYDRO 4 (2' FURYLMETHYL) 6 NITRO 3 OXO 2H 1,4 BENZOXAZINE; 3,4 DIHYDRO 4 (2' FURYLMETHYL) 7 METHYL 3 OXO 2 PROPYL 2H 1,4 BENZOXAZINE; 3,4 DIHYDRO 4 (2' FURYLMETHYL) 7 METHYL 3 OXO 2H 1,4 BENZOXAZINE; 4 BENZYL 3,4 DIHYDRO 7 METHYL 3 OXO 2H 1,4 BENZOXAZINE; 4 BENZYL 6 CHLORO 3,4 DIHYDRO 3 OXO 2 PROPYL 2H 1,4 BENZOXAZINE; 6 CHLORO 2 ETHYL 3,4 DIHYDRO 4 (2' FURYLMETHYL) 3 OXO 2H 1,4 BENZOXAZINE; 6 CHLORO 3,4 DIHYDRO 3 OXO 2 PROPYL 4 (3' PYRIDINYLMETHYL) 2H 1,4 BENZOXAZINE; 6 CHLORO 3,4 DIHYDRO 4 (2' FURYLMETHYL) 2 METHYL 3 OXO 2H 1,4 BENZOXAZINE; 6 CHLORO 3,4 DIHYDRO 4 (2' FURYLMETHYL) 3 OXO 2 PROPYL 2H 1,4 BENZOXAZINE; 6 CHLORO 3,4 DIHYDRO 4 (2' FURYLMETHYL) 3 OXO 2H 1,4 BENZOXAZINE; 6 CHLORO 3,4 DIHYDRO 4 (4' METHOXYBENZYL) 3 OXO 2 PROPYL 2H 1,4 BENZOXAZINE; 6,7,8,9 TETRAHYDRO 4 (2' FURYLMETHYL) 3 OXO 2 PROPYL 2H NAPHTHO[2,3 B][1,4]OXAZINE; 6,7,8,9 TETRAHYDRO 4 (2' FURYLMETHYL) 3 OXO 2H NAPHTHO[2,3 B][1,4]OXAZINE; ALDEHYDE; ALKANOIC ACID; BENZOXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; MICROWAVE COOKING; ONE POT SYNTHESIS; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 33646439837     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.059     Document Type: Article

References (57)

1. Sainsbury M. Oxazines, Thiazines and Their Benzoderivatives. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon, Oxford 995-1038
2. For a recent review on synthesis of 3,4-dihydro-2H-1,4-benzoxazines, see:
3. Ilaš J., Anderluh P.S., Dolenc M.S., and Kikelj D. Tetrahedron 61 (2005) 7325-7348
4. Minami Y., Yoshida K., Azuma R., Saeki M., and Otani T. Tetrahedron Lett. 34 (1993) 2633-2636
5. For designed enediynes, see:
6. Dai W.-M. Curr. Med. Chem. 10 (2003) 2265-2283
7. Niemeyer H.M. Phytochemistry 27 (1988) 3349-3358
8. Kawakita T., Kuroita T., Yasumoto M., Sano M., Inaba K., Fukuda T., and Tahara T. Chem. Pharm. Bull. 40 (1992) 624-630
9. Kuroita T., Sakamori M., and Kawakita T. Chem. Pharm. Bull. 44 (1996) 756-764
10. Kuroita T., Marubayashi N., Sano M., Kanzaki K., Inaba K., and Kawakita T. Chem. Pharm. Bull. 44 (1996) 2051-2060
11. 2 affinity, see:
12. Taverne T., Diouf O., Depreux P., Poupaert J.H., Lesieur D., Guardiola-Lemaïtre B., Renard P., Rettori M., Caignard D., and Pfeiffer B. J. Med. Chem. 41 (1998) 2010-2018
13. Caliendo G., Grieco P., Perissutti E., Santagada V., Santini A., Alberizio S., Fattorusso C., Pinto A., and Sorrentino R. Eur. J. Med. Chem. 33 (1998) 957-967
14. Caliendo G., Perissutti E., Santagada V., Fiorino F., Severino B., d'Emmanuele di Villa Bianca R., Lippolis L., Pinto A., and Sorrentino R. Bioorg. Med. Chem. 10 (2002) 2663-2669
15. Caliendo G., Perissutti E., Santagada V., Fiorino F., Severino B., Cirillo D., d'Emmanuele di Villa Bianca R., Lippolis L., Pinto A., and Sorrentino R. Eur. J. Med. Chem. 39 (2004) 815-826
16. For a review, see:
17. Sebille S., de Tullio P., Boverie S., Antoine M.H., Lebrun P., and Pirotte B. Curr. Med. Chem. 11 (2004) 1213-1222
18. Matsuoka H., Ohi N., Mihara M., Suzuki H., Miyamoto K., Maruyama N., Tsuji K., Kato N., Akimoto T., Takeda Y., Yano K., and Kuroki T. J. Med. Chem. 40 (1997) 105-111
19. Touzeau F., Arrault A., Guillaumet G., Scalbert E., Pfeiffer B., Rettori M., Renard P., and Mérour J.-Y. J. Med. Chem. 46 (2003) 1962-1979
20. Combs D.W., Rampulla M.S., Bell S.C., Klaubert D.H., Tobia A.J., Falotico R., Haertlein B., Lakas-Weiss C., and Moore J.B. J. Med. Chem. 33 (1990) 380-386
21. D'Ambra T.E., Estep K.G., Bell M.R., Eissenstat M.A., Josef K.A., Ward S.J., Haycock D.A., Baizman E.R., Casiano F.M., Beglin N.C., Chippari S.M., Grego J.D., Kullnig R.K., and Daley G.T. J. Med. Chem. 35 (1992) 124-135
22. Bourlot A.-S., Sánchez I., Dureng G., Guillaumet G., Massingham R., Monteil A., Winslow E., Pujol M.D., and Mérour J.-Y. J. Med. Chem. 41 (1998) 3142-3158
23. Largeron M., and Fleury M.-B. Tetrahedron Lett. 39 (1998) 8999-9002
24. Largeron M., Lockhart B., Pfeiffer B., and Fleury M.-B. J. Med. Chem. 42 (1999) 5043-5052
25. Also see:
26. Largeron M., Dupuy H., and Fleury M.-B. Tetrahedron 51 (1995) 4953-4968
27. Largeron M., Neudorffer A., Vuilhorgne M., Blattes E., and Fleury M.-B. Angew. Chem., Int. Ed. 41 (2002) 824-827
28. Blattes E., Fleury M.-B., and Largeron M. J. Org. Chem. 69 (2004) 882-890
29. Itoh K., Kanzaki K., Ikebe T., Kuroita T., Tomozane H., Sonda S., Sato N., Keiichiro H., and Kawakita T. Eur. J. Med. Chem. 34 (1999) 977-989
30. Iakovou K., Kazanis M., Vavayannis A., Bruni G., Romeo M.R., Massarelli P., Teramoto S., Fujiki H., and Mori T. Eur. J. Med. Chem. 34 (1999) 903-917
31. Poupaert J., Carato P., and Colacino E. Curr. Med. Chem. 12 (2005) 877-885
32. Arrault A., Touzeau F., Guillaumet G., Léger J.-M., Jarry C., and Mérour J.-Y. Tetrahedron 58 (2002) 8145-8152
33. For a solid-phase synthesis, see:
34. Lee C.L., Chan K.P., Lam Y., and Lee S.Y. Tetrahedron Lett. 42 (2001) 1167-1169
35. Kundu N.G., Chaudhuri G., and Upadhyay A. J. Org. Chem. 66 (2001) 20-29
36. Henry N., Guillaumet G., and Pujol M.D. Tetrahedron Lett. 45 (2004) 1465-1468
37. Shridhar D.R., Jogibhukta M., and Krishnan V.S.H. Org. Prep. Proced. Int. 14 (1982) 195-197
38. Yamazaki A., Achiwa I., and Achiwa K. Tetrahedron: Asymmetry 7 (1996) 403-406
39. Albanese D., Landini D., and Penso M. Chem. Commun. (1999) 2095-2096
40. Buon C., Chacun-Lefévre L., Rabot R., Bouyssou P., and Coudert G. Tetrahedron 56 (2000) 605-614
41. Torraca K.E., Kuwabe S.-I., and Buchwald S.L. J. Am. Chem. Soc. 122 (2000) 12907-12908
42. Kuwabe S., Torraca K., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 12202-12206
43. Cho S.-D., Park Y.-D., Kim J.-J., Lee S.-G., Ma C., Song S.-Y., Joo W.-H., Falck J.R., Shiro M., Shin D.-S., and Yoon Y.-J. J. Org. Chem. 68 (2003) 7918-7920
44. Dai W.-M., Guo D.-S., and Sun L.-P. Tetrahedron Lett. 42 (2001) 5275-5278
45. Dai W.-M., Sun L.-P., and Guo D.-S. Tetrahedron Lett. 43 (2002) 7699-7702
46. Sun L.-P., Huang X.-H., and Dai W.-M. Tetrahedron 60 (2004) 10983-10992
47. For a microwave-assisted solid-phase indole synthesis, see:. Dai W.-M., Guo D.-S., Sun L.-P., and Huang X.-H. Org. Lett. 5 (2003) 2919-2922
48. Dai W.-M., and Lai K.W. Tetrahedron Lett. 43 (2002) 9377-9380
49. Dai W.-M., Wang X., and Ma C. Tetrahedron 61 (2005) 6879-6885
50. For recent reviews, see:
51. Nüchter M., Ondruschka B., Bonrath W., and Gum A. Green Chem. 6 (2004) 128-141
52. Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284
53. Pottorf R.S., Chadha N.K., Katkevics M., Ozola V., Suna E., Ghane H., Regberg T., and Player M.R. Tetrahedron Lett. 44 (2003) 175-178
54. Compound 4a was reported, see:. Takebayashi T., Iwasawa N., and Mukaiyama T. Bull. Chem. Soc. Jpn. 56 (1983) 1107-1112
55. For a recent example of reductive N-alkylation of a secondary amine with aldehydes under microwave heating, see:. Coats S.J., Schulz M.J., Carson J.R., Codd E.E., Hlasta D.J., Pitis P.M., Stone Jr. D.J., Zhang S.-P., Colburn R.W., and Dax S.L. Bioorg. Med. Chem. Lett. 14 (2004) 5493-5498
56. 3 was reported, see:. Abdel-Magid A.F., Carson K.G., Harris B.D., Maryanoff C.A., and Shah R.D. J. Org. Chem. 61 (1996) 3849-3862
57. 3.