Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
10.15.1.1.4.5.3 Method 3: Acid-Catalyzed Condensation of 1-Arylpyrroles with 2,5-Dimethoxytetrahydrofuran

DOI: 10.1055/sos-SD-010-00864

Gallagher, P. T.Science of Synthesis, (200110707.

9-Arylcarbazoles may be synthesized by reacting 1-arylpyrroles with 2,5-dimethoxytetrahydrofuran in glacial acetic acid, in yields ranging from 22 to 55% (Scheme 23). 1-Phenyl-1H-pyrrole (53) can be made from aniline (1 equiv) and 2,5-dimethoxytetrahydrofuran (54).[‌73‌] Mechanistically the reaction in Scheme 23 goes via initial condensation of 53 with 54 to produce 1-phenylindole. The condensation process is then repeated to produce the 9-phenyl-9H-carbazole (55). The condensation between 2,5-dimethoxytetrahydrofuran (3 equivs) and aniline (1 equiv) also produces 9-arylcarbazoles, albeit in lower yield.

Meeeee 88 Meee-Meeeeeeee Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee 8,8-Meeeeeeeeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8M-eeeeeeeee (88):[‌88‌]

M eeeeeee ee 8-eeeeee-8M-eeeeeee (88; 8.88e, 8eeee) eee 8,8-eeeeeeeeeeeeeeeeeeeeeeee (88; 8.88e, 88eeee) ee eeeeeee MeMM eee eeeeee eeeee eeeeee eee 88e. Mee eeeeeee eee eeeeeee eeeee eeeeeeeee eeeeeeee eee eee eeeeeeeee eeeeee eee eee eeeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeee 88; eeeee: 8.88e (88%); ee 8888°M.

References


Cookie-Einstellungen