Application of DMF-methyl sulfate adduct in the regioselective synthesis of 3-acylated indolizines

Tetrahedron Letters

Volumn 48, Issue 33, 2007, Pages 5739-5742

  Przewloka, Teresa ^a   Chen, Shoujun ^a   Xia, Zhiqiang ^a   Li, Hao ^a   Zhang, Shijie ^a   Chimmanamada, Dinesh ^a   Kostik, Elena ^a   James, David ^a   Koya, Keizo ^a   Sun, Lijun ^a  

^a Synta Pharmaceuticals Corp   (United States)

Author keywords

DMF; Indolizine; Methyl sulfate; Picolinium salt; Regioselective synthesis

Indexed keywords

ESTER; HALIDE; INDOLIZINE DERIVATIVE; METHYL GROUP; N,N DIMETHYLFORMAMIDE; NITRILE; NITRO DERIVATIVE; PICOLINE DERIVATIVE; REAGENT; SULFATE;

ACYLATION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; PURIFICATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 34447507820     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.095     Document Type: Article

References (26)

1. Gundersen L.-L., Charnock C., Negussie A.H., Rise F., and Teklu S. Eur. J. Pharm. Sci. 30 (2007) 26
2. Hagishita S., Yamada M., Shirahase K., Okada T., Murakami Y., Ito Y., Matsuura T., Wada M., Kato T., Ueno M., Chikazawa Y., Yamada K., Ono T., Teshirogi I., and Ohtani M. J. Med. Chem. 39 (1996) 3636
3. Chai W., Breitenbucher J.G., Kwok A., Li X., Wong V., Carruthers N.I., Lovenberg T.W., Mazur C., Wilson S.J., Axe F.U., and Jones T.K. Bioorg. Med. Chem. Lett. 13 (2003) 1767
4. Bermudez J., Fake C.S., Joiner G.F., Joiner K.A., Km F.D., Miner W.D., and Sanger G.J. J. Med. Chem. 33 (1990) 1924-1929
5. Weide T., Arve L., Prinz H., Waldmann H., and Kessler H. Bioorg. Med. Chem. Lett. 16 (2006) 59
6. Teklu S., Gundersen L.-L., Larsen T., Malterud K.E., and Rise F. Bioorg. Med. Chem. 13 (2005) 3127
7. For a review. Shipman M. Sci. Synth. 10 (2001) 745
8. Smith C.R., Bunnelle E.M., Rhodes A.J., and Sarpong R. Org. Lett. 9 (2007) 1169
9. Tielmann P., and Hoenke C. Tetrahedron Lett. 47 (2006) 261
10. Mmutlane E.M., Harris J.M., and Padwa A. J. Org. Chem. 70 (2005) 8055
11. Bora U., Saikia A., and Boruah R.C. Org. Lett. 5 (2003) 435-438
12. Kim M., and Vedejs E. J. Org. Chem. 69 (2004) 6945
13. Matsuda Y., Kahra S., Katou K., Uenura T., and Tamashita K. Heterocycles 60 (2003) 405
14. Katrisky A.R., Qiu G., Yang B., and He H.-Y. J. Org. Chem. 64 (1999) 7618
15. James D.A., Koya K., Li H., Chen S., Xia Z., Ying W., Wu Y., and Sun L. Bioorg. Med. Chem. Lett. 16 (2006) 5164
16. Sun, L.; Koya, K.; Li, H.; Przewloka, T.; James, D.; Chen, S.; Xia, Z.; Liang, G.; Tatsuta, N.; Wu, Y.; Zhou, D.; Korbut, T.; Du, Z.; Ono, M., Abstr. of Papers, 228th ACS National Meeting, Philadelphia, PA, United States, August 22-26, 2004; MEDI-094.
17. Kel'in A.V., Sromek A.W., and Gevorgyan V. J. Am. Chem. Soc. 123 (2001) 2074-2075
18. Park C.-H., Ryabova V., Seregin I.V., Sromek A.W., and Gevorgyan V. Org. Lett. 6 (2004) 1159-1162
19. Kaloko Jr. J., and Hayford A. Org. Lett. 7 (2005) 4305
20. Xia Z., Przewloka T., Koya K., Ono M., Chen S., and Sun L. Tetrahedron Lett. 47 (2006) 8817
21. Chichibabin A.E., and Stepanov F.N. Chem. Ber. 62B (1929) 1068
22. McCombie S.W., Metz W.A., Nazareno D., Shankar B.B., and Tagat J. J. Org. Chem. 56 (1991) 4963
23. Kantlehner W., and Gutbrod H.D. Liebigs Ann. Chem. (1979) 1362
24. Izumi Y., and Fujita T. J. Mol. Catal. A: Chem. 106 (1996) 43
25. Miki Y., Kinoshita H., and Yoshimaru T. Heterocycles 26 (1987) 199
26. Li H., Xia Z., Chen S., Koya K., Ono M., and Sun L. Org. Process Res. Dev. 11 (2007) 246