Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
16.12.1.4.1.1 One-Pot Reaction of Aryl Cyanides with Alkylphosphonates, Aromatic Aldehydes, and Amidines

DOI: 10.1055/sos-SD-116-00063

von Angerer, S.Science of Synthesis Knowledge Updates, (20111117.

An interesting one-pot procedure for the preparation of 4,6-diarylpyrimidines 60 is based on four successive reactions of an aryl cyanide with an alkylphosphonate, an aromatic aldehyde, and an amidine derivative (Scheme 25).[‌70‌] The alkylphosphonate, nitrile, and aldehyde provide the one-carbon fragments. This reaction works quite well with methyl- and ethylphosphonates (yields: 43–73%), but not with larger groups on the phosphonate.

Meeeee 88 8,8-Meeeeeeeeeeeeeeee eeee Meee Meeeeeee, Meeeeee Meeeeeeeeeeeeeeee, Meee Meeeeeeee, eee Meeeeee Meeeeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Me8 M8 Meeee (%) Mee
Me Me Me 88 [‌88‌]
8,8-M8M8M8 8-eeeeeee MM8MM8Me 88 [‌88‌]
8-eeeeeee 8-MeMM8M8 Me 88 [‌88‌]
8-MM8M8 Me MMeMe 88 [‌88‌]
8,8-M8M8M8 8-eeeeeee MMMe 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M 8.8 M eeee ee MeMe ee eeeeee (8.8 eM, 8 eeee) eee eeeee ee eeeeeee ee e eeeeeeeeee eeeeeee eeee ee eeeeeee eeeeeeeeeeeeeeeee (8 eeee) ee eeeee MMM (88 eM) eeeee eeeee ee -88°M. M eeee ee eeeeeee (8 eeee) ee eeeee MMM (8 eM) eee eeeeee eeeee ee eeeeeee. Mee eeeeeeeee eeeeeeeee ee eeee eeeeee eeeeeee eee eeeeee eeeeee ee -88°M eee eeeeeee eee ee eeeeeeeeee 88 eee. M eeee ee eeeeeeee (8 eeee) ee eeeee MMM ee eeeeeee (8 eM) eee eeeeee eeeee (8 eee), eee eee eeeeeeeee eeeeeee eee eeeeeee ee eeee ee ee 8°M (88 eee). M eeeeeee ee eee eeeeeee ee eeeeeeeee (8 eeee) eee eMe8MMe (8 eeee) ee eeeee eeeeeee (8 eM) eee eeeeeeeeee ee eee eeeeeeee eeeeee eee eee eeeeeeeee eeeeeeeeeeeee eeee eee eeeeee eeeeeee ee eeeeee (88 eee). Meeee eeee, eee eeeeeee eee eeeeeeee eee ee eeeeeeeeee 888–888 eee eeeee MMM (eeeeeee/Me8M 8:8) eee MM/MM eeeeeeee eeeeeeeee eee eeeeeee ee eeeeeeee eeeeeeeee (eeeeeee eee eeeeeeee). Mee eeeeeee eee eeee eeeeeeeeeeee ee 88 eM eeeee eeeeeee eeeeeeee, eee eeeeeee eeee MeMMe (88 eM). Mee eeeeeee eeeeeee eee eeeeee eeee eeeee (8 × 88 eM), eeeee (Me8MM8), eeeeeeeeeeee ee ee. 88 eM, eeeeee eeee ee eee eeeeeee, eee eeeeeeeeee eeee eeee Me8M. Mee eeeeeeeee eeeeeeee eeee eeeeeeeee, eeeeee eeee Me8M, eeeeeeeeeeeeee (MeMM), eee eeeee eeeee eeeeeee eeeeeeee ee eeeee eeeeeeeeeeee eeee eeeeeeee.

References


Cookie-Einstellungen