2,3′‐Bis(3‐methylindolyl)methan aus 3‐Methylindol und Formaldehyd

Abstract

3‐Methyl‐2‐(3‐methyl‐3H‐indol‐3‐yl)methyl‐1H‐indol (2) wird als Vorstufe des 3‐Methyl‐2‐(3‐methyl‐1H‐indol‐2‐yl)‐meth(ylid)in‐2H‐indolium‐Kations (3), dem Farbprodukt der Hopkins‐Cole‐Reaktion des 3‐Methylindols, erkannt.

Bis- and Trisindolylmethanes (BIMs and TIMs)

“…A mechanism was proposed based on the Plancher rearrangement. , The first rearrangement involves the usual migration of an arylalkyl group and leads to the formation of 2,2′-BIMs 257 . The second rearrangement involves the hitherto unreported migration of a methyl group, in preference to an arylalkyl group, and leads to the 2,3′-BIMs 258 (Scheme ) …”

Synthesis of a Novel Type of 2,3′‐BIMs via Platinum‐Catalysed Reaction of Indolylallenes with Indoles

“…Due to the high reactivity of indole through the C3p osition, the synthesis of 2,3'-BIMs is fundamentally am ore challenging target for chemists. [9] However,t his framework appearsi nvery interesting alkaloid natural products such as bengacarboline [10a] or yuehchukene ( Figure 1b), [10b] and some efforts have been made towards the synthesis of fused cyclopenta [b]indoles containing the 2,3'-BIM scaffold using mainly acidc atalysis. [11] In our previousw ork, we reported the Pt-catalysed reaction of allenes with indoles to give 3,3'-BIMs( Scheme 1d).…”