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Please login or sign up for a free trial to access the full content. Method 4: Syntheses Based on the Use of Diaminomaleonitrile

DOI: 10.1055/sos-SD-012-00398

Grimmett, M. R.Science of Synthesis, (200212378.

Diaminomaleonitrile (DAMN, 108) is a highly versatile reagent for imidazole synthesis. It can be converted by reaction with a nitrilium triflate into an amidine salt that can be cyclized to form an imidazol-2-amine, it reacts directly with formimidamide, with ortho esters, and, in the form of its imidate, it cyclizes with ammonia or a primary amine. All of these reactions involve formation of the imidazole 15 bond (Section Oxidative cyclization of the Schiff bases formed when diaminomaleonitrile (108) reacts with carbonyl reagents is described as a 12 bond formation (Section

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Meeee 8 Meeeeeeee ee Meeeeeeeeeeeeeeeeee Me Meee Meeeeeeee-8,8-eeeeeeeeeeeeeee[‌888‌‌888‌,‌888‌,‌888‌]

Meeeeee, Meeeeeeeee Meeeeee Meeeee Meeee (%) Mee
MM(MMe)8, eeeeeee, 888°M
MMM8M, eeeeeee, eeee
888 88
MeMM, MMM, 888°M
MMM, MMMe8, 888°M
888 88
Me8M=Me-Me, MMM, ee, 88e 888 88 [‌888‌]
MMMe8, MeMM, eeeeeee, 88°M 888 88 [‌888‌]
Me8M=MMM8M8, eeeeeee, eeee 888 M8=Me 88
M8=Me 88
MeM(MM)MMe, eeeeeee, eeee, 8e 888 88 [‌888‌]

Meeeee 88 Meeeeeee ee Meeeeeeeeeeeeeeeeee Me Meee 8-Meeee-8M-eeeeeeeee-8-eeeeeeeeeee[‌888‌,‌888‌]

Meee 8,8-eeeeeeeeeeeeeeeeeeeee eeeeee eeee eeeeeeeeeeeeeee eeeeeeeee, eee 8M-eeeeeeeee eeeeeeee eeeeeeeee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeee ee 8,8-eeeeeee-8M-eeeeeeeee-8,8-eeeeeeeeeeeeeee.[‌888‌,‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeeee

8-(eeee-Meeeeeeeee)-8M-eeeeeeeee-8,8-eeeeeeeeeeeeee (888):[‌888‌]

Me e eeee ee eeee-eeeee eeeeeeeeee (8.8e, 88eeee) ee MMM (888eM) eee eeeee MMMM (888; 8.8e, 88eeee). Mee eeeeeeeeeee eeee ee eeeee 88°M, eee e eeeeeeeeeee eeeeee. Meeee eeeeeeee eee 88e eee eeeeeeeeeee eee eeeeeeeeee eeeeeeeeeee, eee eee eeeeeeeee eeee eeee eee eeeeeeeeeeeeeee (eeeeee eee, MMMe8) ee eeee eee eeeeeee; eeeee: 8.88e (88%). Meeeeeeeeeeeeeeee (Me8M/eeeeeeeee eeeee) eeee eee eeeeeee ee eeeee eeeeeee; ee 888888°M.

8-(Meeeeeeeee)-8M-eeeeeeeee-8,8-eeeeeeeeeeeeee (888, M8=Me):[‌888‌]

Me e eeeeeeeeee ee MMMM (888; 8.8e, 88eeee) ee eee eeeeeee (888eM) e eeee ee M-(eeeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeeee (8.8e, 88eeee) ee eeeeeee (888eM) eee eeeee eeeeeeee eeee eeeeeeee eeeeeeee. Mee eeeeeee eee eeee eeeeeeee eee 888e, eeeeee, eee eee eeeeeeeeeee eeeeeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 8.88e (88%); ee 888888°M. Meeeeeeee eeeeeeee eeee eee eeeeeeeee:

8-[(Meeeeeeeeeeeee)eeeee]-8M-eeeeeeeee-8,8-eeeeeeeeeeeeee (888, M8=Me); eeeee: 88%.

8-(Meeeeeeeee)-8M-eeeeeeeee-8,8-eeeeeeeeeeeeee (888, M8=8-Mee); eeeee: 88%.

8-{[(8-Meeeeeeeeeee)eeeeeeee]eeeee}-8M-eeeeeeeee-8,8-eeeeeeeeeeeeee (888, M8=8-MeM8M8); eeeee: 88%.

8-{[(8-Meeeeeeeeeeee)eeeeeeee]eeeee}-8M-eeeeeeeee-8,8-eeeeeeeeeeeeee (888, M8=8-MeMM8M8); eeeee: 88%.

8-{[(8-Meeeeeeeeee)eeeeeeee]eeeee}-8M-eeeeeeeee-8,8-eeeeeeeeeeeeee (888, M8=8-M8MM8M8); eeeee: 88%.

8-Meeee-8M-eeeeeeeee-8-eeeeeeeeeee (888):[‌888‌]

M eeeeeee ee MMMM (888; 8e, 88eeee), MMM8M (8eM, 888eeee), eee eeeeee (888eM) eee eeeeeee ee ee eee 88eee, eeee eeeeee eeeee eeeeee eee 8e. Mee eeee eeeee eeee eeeeee eee eeeeeeeee, eeeeee eeee Me8M, eee eeeeeeeee eeeeeeeeee eeee eee M8M. Meeeeeeeeeeee ee eee eeeeeee eeeeeeee eeee eee eeeeeee; eeeee: 8.8e (88%); ee 888°M. Meee eee eeeeeee eee eeeeeeee 8M-eeeeeeeee-8,8-eeeeeeeeeeeee; eeeee: 8.88e (8%); ee >888°M.