Cadogan–Sundberg indole synthesis

Reaction in organic chemistry From Wikipedia, the free encyclopedia

The Cadogan–Sundberg indole synthesis, or simply Cadogan indole synthesis, is a name reaction in organic chemistry that allows for the generation of indoles from o-nitrostyrenes with the use of trialkyl phosphites, such as triethyl phosphite.[1][2][3][4][5][6][7]

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

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

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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