New efficient access to fused (Het)Aryltetrahydroindolizinones via N-acyl iminium intermediates

Tetrahedron

Volumn 66, Issue 25, 2010, Pages 4647-4653

  Chiurato, Matteo ^a   Boulahjar, Rajaa ^a   Routier, Sylvain ^a   Troin, Yves ^b   Guillaumet, Gérald ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

(HET)METHYLTETRAHYDROINDOLIZINONE; .7',8'0,10',10A' TETRAHYDRO 5'H SPIRO[1,3 DIOXOLANE 2,9' PYRIDO[2,3 A]INDOLIZIN] 5' ONE; .7,8,10,10A TETRAHYDROPYRAZINO[2,3 A]INDOLIZINE 5,9 DIONE; 1 ETHOXY 7 METHYL 1H FURO[3,4 B]QUINOLIN 3 ONE; 1 HYDROXY 2 [2 (2 METHYL 1,3 DIOXOLAN 2 YL)ETHYL] 1,2 DIHYDRO 3 PYRROLO[3,4 B]QUINOLIN 3 ONE; 2 [2 (2 METHYL 1,3 DIOXOLAN 2 YL)ETHYL] 1H PYRROLO[3,4 B]QUINOLINE 1,3(2H) DIONE; 3 [((2 (2 METHYL 1,3 DIOXOLAN 2 YL)ETHYL)AMINO)CARBONYL]PYRAZINE 2 CARBOXYLIC ACID; 5B',6',8',9' TETRAHYDRO 11'H SPIRO[1,3 DIOXOLANE 2,7' INDOLIZINO(1,2 B)QUINOLIN] 11' ONE; 5B,6,8,9 TETRAHYDROINDOLIZINO[1,2 B]QUINOLINE 7,11 DIONE; 6 [2 (2 METHYL 1,3 DIOXOLAN 2 YL)ETHYL] 5H PYRROLO[3,4 B]PYRAZINE 5,7(6H) DIONE; 7 HYDROXY 6 [2 (2 METHYL 1,3 DIOXOLAN 2 YL)ETHYL] 6,7 DIHYDRO 5H PYRROLO[3,4 B]PYRIDIN 5 ONE; 7 HYDROXY 6 [2 (2 METHYL 1,3 DIOXOLAN 2 YL)ETHYL] 6,7DIHYDRO 5H PYRROLO[3,4 B]PYRAZIN 5 ONE; 7',8',10',10A' TETRAHYDRO 5'H SPIRO[1,3 DIOXOLANE 2,9' PYR AZINO[2,3 A] INDOLIZIN] 5' ONE; 7,8,10,10A TETRAHYDROPYRIDO[2,3 A]INDOLIZINE 5,9 DIONE; AMIDE; CARBOXYLIC ACID DERIVATIVE; DIETHYLQUINOXALINE 2,3 DICARBOXYLATE; ETHYL 3 FORMYL 6 METHOXYQUINOLIN 2 CARBOXYLATE; ETHYL 3 FORMYL 6 METHYLQUINOLINE 2 CARBOXYLATE; ETHYL 3 FORMYLQUINOXALINE 2 CARBOXYLATE; ETHYL 3 HYDROXY QUINOXALINE 2 CARBOXYLATE; ETHYL 3 TRIFLUOROMETHANESULFONYLOXY QUINOXALINE 2 CARBOXYLATE; INDOLIZINE DERIVATIVE; N [2 (2 METHYL 1,3 DIOXOLAN 2 YL)ETHYL] 5H PYRROLO[3,4 B]PYRIDINE 5,7(6H) DIONE; N ACETYLPYRAZINE 2 CARBOXAMIDE; PYRAZINE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DEPROTECTION REACTION; PRIORITY JOURNAL;

EID: 77953122470     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.100     Document Type: Article

References (39)

1. Alberts B., Johnson A., Lewis J., Raff M., Roberts K., and Walter P. Molecular Cell Biology. 4th ed. (2002), Garland, New York, NY Chapter 17
2. Toogood P.L. Med. Res. Rev. 21 (2001) 487-498
3. Huwe A., Mazitschek R., and Giannis A. Angew. Chem., Int. Ed. 42 (2003) 2122-2138
4. Kong N., Fotouhi N., Wovkulich P.M., and Roberts J. Drugs Future 28 (2003) 881-896
5. Blagden S., and de Bono J. Curr. Drugs Targets 6 (2005) 325-335
6. Shapiro G.I. J. Clin. Oncol. 24 (2006) 1770-1783
7. Honma T., Hayashi Y., Aoyama T., Hashimoto N., Machida T., Fukasawa K., Iwama T., Ikeura C., Ikuta M., Suzuki-Takahashi I., Iwasawa Y., Hayama T., Hishimura S., and Morishima H. J. Med. Chem. 44 (2001) 4615-4627
8. Honma T., Yoshizumi T., Hashimoto N., Hayashi K., Kawanishi K., Fukasawa K., Takaki T., Ikeura C., Ikuta M., Suzuki-Takahashi I., Hayama T., Nishimura S., and Morishima H. J. Med. Chem. 44 (2001) 4628-4640
9. Chiurato M., Routier S., Troin Y., and Guillaumet G. Eur. J. Org. Chem. (2009) 3011-3021
10. Vitry C., Bedat J., Prigent Y., Levacher V., Dupas G., Salliot I., Queguiner G., and Bourguignon J. Tetrahedron 57 (2001) 9101-9108
11. Gribble G.W., Fletcher G.L., Ketcha D.M., and Rajopadhye M. J. Org. Chem. 54 (1989) 3264-3269
12. Hemmerich P., and Fallab S. Helv. Chim. Acta 41 (1958) 498-513
13. Carpino L.A., Xia J., and El-Faham A. J. Org. Chem. 69 (2004) 54-61
14. Blanco M.M., Levin G.J., Shapira C.B., and Perillo I.A. Heterocycles 57 (2002) 1881-1890
15. Zhou Z.L., Navratil J.M., Cai S.X., Whittemore E.R., Espitia S.A., Hawkinson J.E., Tran M., Woodward R.M., Weber E., and Keana J.F.W. Bioorg. Med. Chem. 9 (2001) 2061-2071
16. Othman M., Pigeon P., and Decroix B. Tetrahedron 53 (1997) 2495-2504
17. ®) has been also used for this kind of reaction, see:. Padwa A., and Brodney M.A. Arkivoc vi (2002) 35-48
18. Buckland P.R. J. Heterocycl. Chem. 17 (1980) 397-398
19. This transformation occurred even though the silica gel was washed with triethylamine in order to suppress the residual acidity. See Experimental section.
20. Hitchins G.J., and Vernon J.M. J. Chem. Soc., Perkin Trans. 1 (1990) 1757-1763
21. Muth M., Bender W., Scharfenstein O., Holzgrabe U., Balaktova E., Trankle C., and Mohr K. J. Med. Chem. 46 (2003) 1031-1040
22. Ganjian I., Khorshidi M., and Lalezari I. J. Heterocycl. Chem. 28 (1991) 1173-1175
23. Tsuda T., Fujishima K., and Ueda H. Agric. Biol. Chem. 45 (1981) 2129-2130
24. Schreier, H.; Gonzalez-Rothi, R. PCT Int. Appl. 199105771.
25. Goto T., Konno M., Saito M., and Sato R. Bull. Chem. Soc. Jpn. 62 (1989) 1205-1210
26. Maulding D.R. J. Heterocycl. Chem. 25 (1988) 1777-1779
27. Rebstock A.S., Mongin F., Trécourt F., and Queguiner G. Tetrahedron Lett. 43 (2002) 767-769
28. Doehner R. F. Jr. US Patent 4910327 A (20/03/1990); 4925944 A (15/05/1990); 5892050 A (06/04/1999).
29. Anderson K.W., and Dalvie D.K. J. Heterocycl. Chem. 30 (1993) 1533-1536
30. Huo M., Kuang Y.Y., and Chen F.E. Org. Prep. Proced. Int. 36 (2004) 331-336
31. Gräf E., and Troschütz R. Synthesis (1999) 1216-1222
32. Lou R., VanAlstine M., Sun X., and Wentland P.M. Tetrahedron Lett. 44 (2003) 2477-2480
33. Gibson K.R., Hitzel L., Russell J., Mortishire-Smith J., Gerhard U., Gelley R.A., Reeve A., Rowley M., Nadin A., and Owens A.P. J. Org. Chem. 67 (2002) 9354-9360
34. Monge A., Palop J.A., Del Castillo J.C., Caldero J.M., Roca J., Romero G., Del Rio J., and Lasheras B. J. Med. Chem. 36 (1993) 2745-2750
35. Eller G.A., Datterl B., and Holzer W. J. Heterocycl. Chem. 44 (2007) 1139-1143
36. Haldar P., Dutta B., Guin J., and Ray J.K. Tetrahedron Lett. 48 (2007) 5855-5857
37. Chattaway F.D., and Humphrey W.S. J. Chem. Soc. (1929) 645-651
38. Here too, increasing time of reflux or amount of acid did not introduce changes to the corresponding yield.
39. Morgan D.O., Ollis D.W., and Stanforth S.P. Tetrahedron 56 (2000) 5523-5534