Details

Autor(en) / Beteiligte

• Ansari, Nurul H
• Dacko, Christopher A
• Akhmedov, Novruz G
• Söderberg, Björn C. G

Titel

Double Palladium Catalyzed Reductive Cyclizations. Synthesis of 2,2′‑, 2,3′‑, and 3,3′-Bi‑1H‑indoles, Indolo[3,2‑b]indoles, and Indolo[2,3‑b]indoles

Ist Teil von

• Journal of organic chemistry, 2016-10, Vol.81 (19), p.9337-9349

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2016

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A palladium catalyzed, carbon monoxide mediated, double reductive cyclization of 1,4-, 1,3-, and 2,3-bis­(2-nitroaryl)-1,3-buta­dienes to afford 2,2′-, 2,3′-, and 3,3′-biindoles, respectively, was developed. In contrast, reductive cyclizations of 1,2-bis­(2-nitro­aryl)­ethenes were nonselective, affording mixtures of monocyclized indoles, indolo­[3,2-b]­indole, indolo­[1,2-c]­quinazolin-6­(5H)-ones, and 5,11-dihydro-6H-indolo­[3,2-c]­quinolin-6-ones. Nonselective product formation was also observed from reductive cyclization of 1,1-bis­(2-nitro­aryl)­ethenes, producing indolo­[2,3-b]­indoles and indolo­[2,3-c]­quinolin-6-ones. Carbon monoxide insertion to give the carbonyl containing products was the major or sole reaction path starting from 1,1- or 1,2-bis­(2-nitro­aryl)­ethenes.