2,2 '-Biindolyl Reactions with Aldehydes

• 2,2'-Biindolyl has been condensed with aromatic and aliphatic aldehydes and products featuring 10-membered rings have been obtained. Thus, benzaldehyde gave compound 24a as the primary product, which readily underwent transannular oxidative coupling to 25a. The structures of both compounds were confirmed by X-ray crystallography. The product from 2,2'-biindolyl and formaldehyde under strongly acidic conditions was slightly different leading to compound 11, whose structure also was confirmed by X-ray crystallography. In this case, two molecules of 2,2'-biindolyl reacted with six molecules of formaldehyde.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Keyword

Transannular reactions

Nitrogen heterocycles

Dehydrogenation

Carbocycles

Macrocycles

Aldehydes

Publication and Content Type

ref (subject category)

art (subject category)