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- Title
Synthesis of Indoles by Domino Reaction of 2-(Tosylamino)benzyl Alcohols with Furfurylamines: Two Opposite Reactivity Modes of the α-Carbon of the Furan Ring in One Process.
- Authors
Uchuskin, Maxim G.; Molodtsova, Natalia V.; Lysenko, Sergey A.; Strel'nikov, Vladimir N.; Trushkov, Igor V.; Butin, Alexander V.
- Abstract
An unusual domino reaction where the same furan α-carbon atom reacts initially as a nucleophile and then as an electrophile is reported. In the presence of acid, N-tosylfurfurylamines react with 2-(tosylamino)benzyl alcohols to afford 2-(2-acylvinyl)indoles. The reaction proceeds by Friedel-Crafts alkylation at the C(2) atom of furan followed by acid-catalyzed intramolecular nucleophilic attack of the ortho-amino group onto the same carbon atom. The replacement of the tosylamino leaving group by phthalimide enables generation of a different type of indole yet allows the ambiphilic nature of C(2) to be retained. Both types of indoles were obtained when N-furfurylbenzamides were employed.
- Subjects
FURANS synthesis; NUCLEOPHILES; AMINES; ALKYLATION; AMINO group
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 12, p2508
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301762