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Please login or sign up for a free trial to access the full content. Method 2: By Carbon Nucleophiles via Nucleophilic Substitution

DOI: 10.1055/sos-SD-016-00385

Haider, N.; Holzer, W.Science of Synthesis, (200416348.

The reaction of 1-chlorophthalazine (107) with active methylene compounds such as ethyl cyanoacetate, diethyl malonate, malononitrile, or benzyl cyanide under the influence of a strong base gives the corresponding C-substituted phthalazines 108 (Scheme 45).[‌288‌] Similarly, the methylsulfonyl (mesyl) group in 1-mesylphthalazines[‌289‌‌291‌] such as, for instance, in 1-mesyl-4-phenylphthalazine (109)[‌290‌,‌291‌] can be replaced by carbon nucleophiles derived from various CH-acidic compounds to afford substitution products 110 (Scheme 45).

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Meeeee 88 Meeeeeeee ee 8-Meeee-8-eeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 88

Me8 M8 Meeeeeee Meee (eee) Meeee (%) ee (°M) Mee
Me Me 88 88 888888 [‌888‌]
Me 8-Mee 88 88 888888 [‌888‌]
8-MeM8M8 8-Mee 88 88 888888 [‌888‌]
8-MeM8M8 8-Mee 88 88 888888 [‌888‌]
8-Mee 8-Mee 88 88 888888 [‌888‌]
8-MeMM8M8 8-Mee 88 88 888888.8 [‌888‌]
8-eeeee 8-Mee 88 88 888888 [‌888‌]
8-eeeeeee 8-Mee 88 88 888.8888.8 [‌888‌]

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Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeee ee Meeeee Meeee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeee-8-eeeeeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

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8-Meee-8-(8-eeeeeeeeeeeeeee-8-ee)eeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Meeeee M: Me e eeeeeeee eee eeeeeeeeee eeeee-eeeeeee eeeeeee ee 888 (888ee, 8.88eeee, 8 eeeee) eee eeeeeeeeeee eeee 888 (8.88eeee, 8.88 eeeee) ee 8,8-eeeeeee (88eM) eee eeeee Me8MM8 (8.88e, 8.88eeee, 8 eeeee), eee eee eeeeee eee eeeeeeee eeeee. Meee, Me8(eee)8 (88ee, 8.888eeee, 8.888 eeeee) eee e-Me8M (88μM, 8.88eeee, 8.88 eeeee) eeee eeeee eeeeeeeeeeee. Meeee eeeeeee ee 888°M eee 88e, eee eeeeeee eee eeeeeee ee eeeee, eee eeeeeee eee eeeeeee eeee M8M (88eM), eee eeeeeeeee eeee MeMMe (8×8eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M (8×8eM) eee eeeeeeeeeeee ee eeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/MeMM/Me8M 8:8:8) ee eeeee eeeeeeeee 888 ee eeeeeeeee ee eeeeee eeee. Mee eeeeeeeeeeeee eeeeeeeeeeeeee eeee eeeeeeee ee eeeeeeee eee eeee eeeee, eeeeeeeee ee Me8M eee/ee MeMMe, eeee eeeeeee MMe ee eeee 88% ee MMe (8.8 eeeee). Mee eeeeeeeee eeeeee eeee eeeeeeeeeeeeee (eMeMM/Me8M).

Meeeee M: Mee eeeeeeeee eee eeeeeee ee eeeeee M eeeeee eee eee eeeeeee (eeeeeee, 88eM), eeee [8M Me8MM8 ee MeMM (8.8eM, 8.88eeee, 8.88 eeeee)], eee eeeeeeee [Me(MMe8)8 (888ee, 8.8eeee, 8.888 eeeee)] eeee.