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Cadogan–Sundberg indole synthesis

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Reaction in organic chemistry

Cadogan–Sundberg indole synthesis
Named after	John Cadogan Richard J. Sundberg
Reaction type	Ring forming reaction
Identifiers
RSC ontology ID	RXNO:0000509

TheCadogan–Sundberg indole synthesis, or simplyCadogan indole synthesis, is aname reaction inorganic chemistry that allows for the generation ofindoles from o-nitrostyrenes with the use of trialkyl phosphites, such astriethyl phosphite.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

Mechanism

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o-nitrostyrene first reacts with triethyl phosphite, and the nitro group is converted to a nitroso group. The nitroso group then reacts with the alkene, and N-hydroxylindole is formed, which reacts again with triethyl phosphite to form the indole.^[1]^[2]^[3]^[4]

Application

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The Cadogan–Sundberg indole synthesis has been used as an intermediate step in the total synthesis of Tjipanazole E,^[8] transforming 2-[trans-2-[5-Chloro-2-nitrophenyl)vinyl]-5-chloro-1H-indole to 5,5’-Dichloro-2,2’-biindole.

References

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^^a ^bCadogan, John Ivan George; Mackie, R. K. (1974). "Tervalent phosphorus compounds in organic synthesis".Chemical Society Reviews.3 (1):87–137.doi:10.1039/CS9740300087.
^^a ^bWang, Zerong (15 September 2010).Comprehensive Organic Name Reactions and Reagents.doi:10.1002/9780470638859.conrr128.ISBN 9780470638859.
^^a ^bSundberg, Richard J.; Yamazaki, Toshio (1 February 1967). "Rearrangements and ring expansions during the deoxygenation of β,β-disubstituted o-nitrostyrenes".The Journal of Organic Chemistry.32 (2):290–294.doi:10.1021/jo01288a009.
^^a ^bSundberg, Richard J. (1 November 1965). "Deoxygenation of Nitro Groups by Trivalent Phosphorus. Indoles from o-Nitrostyrenes".The Journal of Organic Chemistry.30 (11):3604–3610.doi:10.1021/jo01022a006.
^Gribble, Gordon W. (17 June 2016). "Cadogan–Sundberg Indole Synthesis".Indole Ring Synthesis: From Natural Products to Drug Discovery. pp. 266–277.doi:10.1002/9781118695692.ch26.ISBN 9781118695692.
^Majgier-Baranowska, Helena; Williams, John D.; Li, Bing; Peet, Norton P. (1 February 1967). "Studies on the mechanism of the Cadogan–Sundberg indole synthesis".Tetrahedron Letters.53 (35):4785–4788.doi:10.1016/j.tetlet.2012.06.146.
^Li, Jie Jack (4 January 2014). "Cadogan–Sundberg indole synthesis".Indole Ring Synthesis: From Natural Products to Drug Discovery. Springer. p. 102-103.doi:10.1007/978-3-319-03979-4_49.ISBN 978-3-319-03979-4.
^Kuethe, Jeffrey T.; Wong, Audrey; Davies, Iaan W. (3 September 2003). "Effective Strategy for the Preparation of Indolocarbazole Aglycons and Glycosides: Total Synthesis of Tjipanazoles B, D, E, and I".Organic Letters.5 (20):3721–3723.doi:10.1021/ol035418r.PMID 14507214.