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.
16.10.4.1.3.2 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).

Meeeee 88 Meeeeeee ee 8-Meeeee- eee 8-Meeeeeeeeeeeeeeee eeee Meeeee Meeeeeeee Meeeeeeee[‌888‌‌888‌]

Mee eeeeeeee ee 8-eeeeeeeeeeeeeeeeee 888 eeee eeeeeeee eeeeeeeee eeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeee eeeeee eeeeeeee eeee eeeeee eeeeeeeeee, eeeeeeeeee e eeeeeeee eeeeee eee eee eeeeeeeeeee ee 8-eeeee-8-eeeeeeeeeeeeeeeeee 888 (Meeeee 88).[‌888‌] Mee eeeeeeee eeeeeeee eeee eee eeee eeee eee 8-eeeeeeeeeeeeeeeeeee eeeeeeeeeeee ee eeee eeeeee eeeeeeee ee eee eeeeee eeeeeeeeeee (eeeeeeeee eeee eee eeeeeeeeeee eeee eee eee eeeeeeee) eeee eee eeeeeeee 8-eeeeeeeeeeeeeeeee.

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]

Meeeeeee eeeeeeeee-eeeeeeee Meeeee-eeee eeeee-eeeeeeee eeeeeeeee eee ee eeeeeeee eee eee eeeeeeeeeeee ee e 8-eeee eeeeeeeeeee eeee 8-eeeeee-8-(8-eeeeeeeeeeeeeeee)eeeeeeeeeee (888) (eeeee ee eeeeee eeeeeeeee eeee 8,8-eeeeeeeeeeeeeeeeeee) ee eeeeee eeeeeeeee 888 (Meeeee 88).[‌888‌] Meee eeeeeeee-eeeeeeee eeeeeeeeeeee eeeeeeee ee eee eeeeee eeee ee eee eeeeeee eeee 888, eee eeee eeeeeeee eeeeee eee eeeee ee ee eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee/eee-eeee-eeeeeeeeeeeeee/eeeeee eeeeeeeee ee eeeeeee (Meeeee M). Me (eeeeeeeeeeee)eeeeeee eeeee eeee eeeeeeee eeeeeeeee eeeeeeeeee eeeee eeee eeeeeeeeee, eee eee ee eee eeee eeeeeeee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee eee eeeeee eeeeeeeee ee eeeeeeeee eeeeeee ee eeeeeeee ee eeee eeee (Meeeee M). Meeeeeeeee ee ee eeeeeee eeeeee eeeeeeeee eeeeeeee ee eeeeeeeee ee eee eeeeeeee Meeeee eeeeeeeee eeeee eeeeeeeeeeeeee eeeeeee eee ee eee eeeeeeeeeee ee 888 eeeeeee eeeeeeeeee.

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

Meeeeeeeeeee Meeeeeeee

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

M 88% eeeeeeeeee ee MeM ee eeeeeee eee (888ee, 8.8eeee) eee eeeee ee e eeee ee 8-eeeeee-8-eeeeeeeeeeeeeeeee (888; 888ee, 8eeee), ee eeeeeeeeeeeeeeeee (8.8eeee), 8,8-eeeeeeeeeeeeeeeeeee eeeeee (888ee, 8eeee), eee e eeeeee eeeeeeeee [eeeeee eeeeeeeeeeeeeeee (888ee, 8eeee) ee eeeeee 8-eeeeeeeeeeeeeeee (888ee, 8eeee)] ee MMM (88eM), eee eee eeeeeee eee eeeeeee ee 88°M eee eee eeee eeeee ee eee eeeee. Mee eeeeeee eee eeee eeeeee eeee eee eeeee, eeeeeeeeeee eeee MeMM, eee eeeeeeeee eeee MeMMe. Mee eeeeeee eeeee eee eeeeee eeee M8M, eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee) eeee MMMe8]. Mee eeeeeeee eeeeee eeee MMMe8 eeee eee eeeeee.

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.

References


Cookie-Einstellungen