Rapid entry into heterocycle-fused benzylic azepines and azocines via directed metallation/ring-closing metathesis

Tetrahedron Letters

Volumn 54, Issue 32, 2013, Pages 4254-4258

  Moss, Thomas A ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Azepine; Azocine; Bicycle; Heterocycle; Metathesis

Indexed keywords

AZEPINE DERIVATIVE; AZOCINE DERIVATIVE; BENZILIC ACID; HETEROCYCLIC COMPOUND; RUTHENIUM;

ARTICLE; METALLATION; RING CLOSING METATHESIS; SYNTHESIS; TAUTOMERIZATION;

EID: 84879844351     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.05.142     Document Type: Article

References (23)

1. G.-Q. Chen, J.-H. Xie, D.-H. Bao, S. Liu, and Q.-L. Zhou Org. Lett. 14 2012 2714
2. C. Peng, B. Xu, L.-F. Zhang, M. Ding, X.-J. Han, J. Li, G.-B. Zhang, Y.-Q. Tu, and C.-A. Fan Angew. Chem., Int. Ed. 50 2011 8161
3. J.G. Kettle, D. Roberts, and J.A. Joule Heterocycles 82 2010 349
4. M.-L. Bennasar, E. Zulaica, D. Sole, T. Roca, D. Garcia-Diaz, and S. Alonso J. Org. Chem. 74 2009 8359
5. C.T. Peng, D.S. Yi, J. Feng, H.F. Jian, L.Y. Jiang, L. Xiao, H.P. Jiang, L.L. Ya, L. Zhang, B. Hu, Y. Zhou, Q.L. Fang, B.F. Bei, G.L. Li, S.G. Ai, H.S. Gao, H.S. Wei, and T.M. Xian J. Med. Chem. 53 2010 8140
6. A.K. Ganguly, S.S. Alluri, D. Caroccia, D. Biswas, C.-H. Wang, E. Kang, Y. Zhang, A.T. McPhial, S.S. Carroll, C. Burlein, V. Munshi, P. Orth, and C. Strickland J. Med. Chem. 54 2011 7176
7. L. Benati, B. Nanni, C. Sangiorgi, and P. Spagnolo J. Org. Chem. 64 1999 7836
8. F. Homsi, and G. Rousseau J. Org. Chem. 63 1998 5255
9. R. Ortega, E. Ravina, C.F. Masaguer, F. Areias, J. Brea, M.I. Loza, L. Lopez, J. Selent, M. Pastor, and F. Sanz Bioorg. Med. Chem. Lett. 19 2009 1773
10. For a review, see: S.K. Chattopadhyay, S. Karmakar, T. Biswas, K.C. Majumdar, H. Rahaman, and B. Roy Tetrahedron 63 2007 3919 and references therein
11. T.A. Moss, B.R. Hayter, I.A. Hollingsworth, and T. Nowak Synlett 23 2012 2408
12. T.A. Moss Tetrahedron Lett. 54 2013 993
13. For recent examples see: D.B. Ramachary, and V.V. Narayana Eur. J. Org. Chem. 2011 3514
14. D. Ghosh, L. Thander, S.K. Ghosh, and S.K. Chattopadhyay Synlett 2008 3011
15. S. Kotha, and V.R. Shah Eur. J. Org. Chem. 6 2008 1054
16. For examples of pyrimido-fused azepines by RCM, see: L.E. Kaïm, L. Grimaud, and J. Oble J. Org. Chem. 72 2007 5835
17. K.C. Majumdar, S. Mondal, and D. Ghosh Synthesis 2010 1176
18. C. Lane, and V. Snieckus Synlett 2000 1294
19. M. Stefinovic, and V. Snieckus J. Org. Chem. 63 1998 2808
20. For a review, see: B. Haag, M. Mosrin, H. Ila, V. Malakhov, and P. Knochel Angew. Chem., Int. Ed. 50 2011 9794
21. R. Rios, C. Jimeno, P.J. Carroll, and P.J. Walsh J. Am. Chem. Soc. 124 2002 10272
22. M.V. Nora de Souza, and R.H. Dodd Heterocycles 47 1998 811
23. M. Abarbri, J. Thibonnet, L. Bérillon, F. Dehmel, M. Rottländer, and P. Knochel J. Org. Chem. 65 2000 4618