Abstract
The Cadogan reaction refers to the deoxygenation of o-nitrostyrenes 1 or o-nitrostilbenes with trialkyl phosphite or trialkylphosphine and subsequent cyclization of the resulting intermediate nitrene 2 to form indoles 3.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Cadogan, J. I. G.; Cameron-Wood, M. Proc. Chem. Soc. 1962, 361.
Sundberg, R. J. J. Org. Chem. 1965, 30, 3604–3610.
Scott, T. L.; Söderberg, B. C. G. Tetrahedron Lett. 2002, 43, 1621–1624.
Kuethe, J. T.; Wong, A.; Qu, C.; Smitrovich, J.; Davies, I. W.; Hughes, D. L. J. Org. Chem. 2005, 70, 2555–2567.
Freeman, A. W.; Urvoy, M.; Criswell, M. E. J. Org. Chem. 2005, 70, 5014–5019.
Balaji, G.; Shim, W. L.; Parameswaran, M.; Valiyaveettil, S. Org. Lett. 2009, 11, 4450–4453.
Li, B.; Pai, R.; Cardinale, S. C.; Butler, M. M.; Peet, N. P.; Moir, D. T.; Bavari, S.; Bowlin, T. L. J. Med. Chem. 2010, 53, 2264–2276.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Li, J.J. (2014). Cadogan–Sundberg indole synthesis. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_49
Download citation
DOI: https://doi.org/10.1007/978-3-319-03979-4_49
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-03978-7
Online ISBN: 978-3-319-03979-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)