Mercurous chloride catalyzed Mannich condensation of terminal alkynes with secondary amines and aldehydes

Chinese Journal of Chemistry

Volumn 23, Issue 8, 2005, Pages 1076-1080

  Li, Pin Hua ^a   Wang, Lei ^a,b  

^a HUAIBEI NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

aminoalkyne; Aldehyde; Mannich reaction; Mercurous chloride; Secondary amine; Terminal alkyne

Indexed keywords

EID: 25144499128     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.200591076     Document Type: Article

References (23)

1. (a) Tramonitini, M.; Angiolini, L. Mannich-Bases, Chemistry and Uses, CRC Press, Boca Raton, FL, 1994.
2. (b) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1045.
3. (c) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235.
4. (d) Allef, P.; Kunz, H. Tetrahedron: Asymmetry 2000, 11, 375.
5. (a) McNally, J. J.; Youngman, M. A.; Dax, S. L. Tetrahedron Lett. 1998, 39, 967.
6. (b) Youngman, M. A.; Dax, S. L. Tetrahedron Lett. 1997, 38, 6347.
7. (a) Adams, T. C.; Dupont, A. C.; Carter, J. P.; Kachur, J. F.; Guzewska, M. E.; Rzeszotarski, W. J.; Farmer, S. G.; Noronha-Blob, L.; Kaisen, C. J. Med. Chem. 1991, 34, 1585.
8. (b) Sanders, K. B.; Thomas, A. J.; Pavia, M. R.; Davis, R. E.; Coughenour, L. L.; Myers, S. L.; Fischer, S.; Moos, W. H. Bioorg. Med. Chem. Lett. 1992, 2, 803.
9. (a) Zhang, H. C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 3449.
10. (b) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647.
11. (c) Arnold, H.; Overman, L. E.; Sharp, M. J.; Witschel, M. C. Org. Synth. 1992, 70, 111.
12. (d) Overman, L. E.; Rodriguez-Campos, I. M. Synlett 1992, 995.
13. (a) Mannich, C.; Chang, F. T. Ber. 1933, 66B, 418.
14. (b) Leadbeater, N. E.; Torenius, H. M.; Tye, H. Mol. Div. 2003, 7, 135.
15. (c) Youngman, M. A.; Dax, S. L. J. Comb. Chem. 2001, 3, 469.
16. (d) Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem. Eur. J. 2003, 9, 2797.
17. Shi, L.; Tu, Y. Q.; Wang, M.; Zhang, F. M.; Fan, C. A. Org. Lett. 2004, 6, 1001.
18. (a) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron Lett. 2001, 42, 6049.
19. (b) Kabalka, G. W.; Wang, L.; Pagni, R. M. Synlett 2001, 676.
20. (c) Wang, L.; Li, P. Chin. J. Chem. 2003, 21, 710.
21. (a) Wei, C.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584.
22. (b) Wei, C.; Li, Z.; Li, C. J. Org. Lett. 2003, 5, 4473.
23. Katritzky, A. R.; Gallos, J. K.; Yannakopoulou, K. Synthesis 1989, 31.