Weinreb amide based synthetic equivalents for convenient access to 4-aryl-1,2,3,4-tetrahydroisoquinolines

Tetrahedron

Volumn 66, Issue 21, 2010, Pages 3723-3729

  Kommidi, Harikrishna ^a   Balasubramaniam, Sivaraman ^a   Aidhen, Indrapal Singh ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

4 Aryl tetrahydroisoquinoline; Acid promoted cyclization; Grignard addition; Weinreb amide

Indexed keywords

4 ARYL 1,2,3,4 TETRAHYDROISOQUINOLINE; ACID; AMIDE; BENZENESULFONIC ACID DERIVATIVE; GLYCINAMIDE; MAGNESIUM SALT; N METHOXY N METHYL N' PHENYLSULFONYL GLYCINAMIDE; N METHOXY N METHYL N'BENZYL N' TERT BUTYLOXY CARBONYL GLYCINAMIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TETRAHYDROISOQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; CHEMICAL REACTION; CYCLIZATION; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 77951099000     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.074     Document Type: Article

References (37)

1. Rozwadowska M.D. Heterocycles 39 (1994) 903
2. Jacob J.N., and Nichols D.E. J. Med. Chem. 24 (1981) 1013
3. Maryanoff B.E., McComsey D.F., Gardocki J.F., Shank R.P., Costanzo M.J., Nortey S.O., Schneider C.R., and Setler P.E. J. Med. Chem. 30 (1987) 1433
4. Chesworth R., Zawistoski M.P., Lefker B.A., Cameron K.O., Day R.F., Mangano F.M., Rosati R.L., Colella S., Petersen D.N., Brault A., Lu B., Pan L.C., Perry P., Ng O., Castle-berry T.A., Owen T.A., Brown T.A., Thompson D.D., and DasilvaJardine P. Bioorg. Med. Chem. Lett. 14 (2004) 2729
5. Wanner K.T., Beer H., Hoefner G., and Ludwig M. Eur. J. Org. Chem. 9 (1998) 2019
6. Brossi A., Grethe G., Teitel S., Wildman W.C., and Bailey D.T. J. Org. Chem. 35 (1970) 1100
7. Prat L., Bureau R., Daveu C., Levacher V., Dupas G., Que-guiner G., and Bourguignon J. J. Heterocycl. Chem. 37 (2000) 767
8. Schwartz M.A., and Scott S.W.A. J. Org. Chem. 36 (1971) 1827
9. Pridgen L.N., Kilmer L.B., and Webb R.L. J. Org. Chem. 47 (1982) 1985
10. Coote S.J., Davies S.G., Middlemiss D., and Naylor A. J. Chem. Soc., Perkin Trans. 1 (1989) 2233
11. Hara H., Shirai R., Hoshino O., and Umezawa B. Heterocycles 20 (1983) 1945
12. Zara-Kaczian E., Deak G., Szollosy A., and Brlik J. Acta Chim. Hung. 127 (1990) 743
13. Toda J., Sonobe A., Ichikawa T., Saitoh T., Horiguchi Y., and Sano T. ARKIVOC 1 (2000) 165
14. Bates H.A. J. Org. Chem. 46 (1981) 4931
15. Bates H.A. J. Org. Chem. 48 (1983) 1932
16. Bates H.A., Bagheri K., and Vertino P.M. J. Org. Chem. 51 (1986) 3061
17. Katakawa J., Yoshimatsu H., Yoshida M., Zhang Y., Irie H., and Yajima H. Chem. Pharm. Bull. 36 (1988) 3928
18. Ruchirawat S., Tontoolarug S., and Sahakitpichan P. Heterocycles 55 (2001) 635
19. Kihara M., Kashimoto M., and Kobayashi Y. Tetrahedron 48 (1992) 67
20. China Raju B., Neelakantan P., and Bhalerao U.T. Tetrahedron Lett. 45 (2004) 7487
21. Seijas J.A., Vazquez-Tato M.P., Martinez M.M., and Pizzolatti M.G. Tetrahedron Lett. 46 (2005) 5827 and references cited therein
22. Deng X., Liang J.T., Liu J., McAllister H., Schubert C., and Mani N.S. Org. Process Res. Dev. 11 (2007) 1043
23. Sivaraman B., Senthilmurugan A., and Aidhen I.S. Synlett (2007) 2841
24. Sivaraman B., and Aidhen I.S. Synlett (2007) 959
25. Manjunath B.N., Sane N.P., and Aidhen I.S. Eur. J. Org. Chem. (2006) 2851
26. N-Methoxy- N-methyl amides are popularly called as Weinreb amides. For a review on Weinreb amide chemistry see:
27. Sivaraman B., and Aidhen I.S. Synthesis (2008) 3723
28. Singh J., Satyamurthi N., and Aidhen I.S. J. Prakt. Chem. 342 (2000) 340
29. Mentzel M., and Hoffmann H.M.R. J. Prakt. Chem. 339 (1997) 517
30. Sibi M.P. Org. Prep. Proceed. Int. 25 (1993) 15
31. Mickel S.J., Niederer D., Daeffler R., Osmani A., Kuesters E., Schmid E., Schaer K., Gamboni R., Chen W., Loeser E., Kinder Jr. F.R., Konigsberger K., Prasad K., Ramsey T.M., Repic O., Wang R.M., Florence G., Lyothier I., and Paterson I. Org. Process Res. Dev. 8 (2004) 122
32. El-Sharief A.M., Ammar Y.A., Zahran M.A., Ali A.H., and El-Gaby M.S. Molecules 6 (2001) 267
33. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 2nd ed. (1991), John Wiley & Sons,, New York, NY p 379
34. Coffin A.R., Rousell M.A., Tserlin E., and Pelkey E.T. J. Org. Chem. 71 (2006) 6678 Observing difficulties with the use of DCC mentioned in this report for the carboxyl activation, we resorted to activation by simpler, mixed anhydride method
35. Raghuram T., Vijaysaradhi S., Aidhen I.S., and Singh J. Synth. Commun. 29 (1999) 3215
36. Bulman P.C., Leach D.C., Hayman C.M., Hamzah A.S., Allin S.M., and McKee V. Synlett (2003) 1025
37. Watson S.C., and Eastham J.F. J. Organomet. Chem. 9 (1967) 165