Science of Synthesis

Haider, N.; Holzer, W., Science of Synthesis, (2004) 16, 219.

(Hydroxymethyl)pyridazines can be oxidized to the corresponding aldehydes or carboxylic acids, depending on the choice of the oxidant. With manganese(IV) oxide[‌336‌] or dimethyl sulfoxide/oxalyl chloride,[‌261‌] the aldehyde is obtained, whereas employment of potassium permanganate[‌640‌] or potassium dichromate[‌430‌] affords the acid. Replacement of the hydroxy group by other functionalities is usually achieved by transformation into an appropriate halide which, in turn, can undergo nucleophilic substitution reactions.[‌35‌,‌333‌,‌392‌] These concepts are illustrated (‌Scheme 71‌) by transformation of the (hydroxymethyl)pyridazine ‌184‌ into the aldehyde ‌116‌ [oxidation with manganese(IV) oxide] and the bromide ‌185‌ (reaction with carbon tetrabromide/triphenylphosphine).

‌Meeeee 88‌ Meeeeeeeeeee ee e (Meeeeeeeeeeee)eeeeeeeeee[‌888‌,‌888‌]

Meeee(eeeeeeeeeee)eeeeeeeee ee eeee ee eeee(eeeeeeeeeee)eeeeeeeee eee ee eeeeee eeeeeeee ee eeeeeee eeee eeeeeeeee(MM) eeeee,[‌888‌] eeeeeeeeee eeeeeeeeeeeeee,[‌888‌] ee eeeeeeeee eeeeeeeeeeee.[‌888‌] Me eee eeeee eeee, eeeeee(eeeeeeeee-8-ee)- ee eeee ee eeeeee(eeeeeeeee-8-ee)eeeeeeeee eeeeeee eeeeeeeee eeeeeee eeeeeeeeeeeeeeeeee, eeeeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeee- eee eeeeeee-eeeeeeeeeee eeeeeeeeeee.[‌888‌,‌888‌] Meee, ee eeeeeeeeee, eeee-eeeeeee eeeeeeeeee/eeeeeeee eeee eeeeeeeeeeeeee eee eeee eeeeeeee eee eeeeee(eeeeeeeee-8-ee)eeeeeeee.[‌888‌] Meeeeeee, eee eeeeeeeee eeeeeee eeee eeee eeeeeeee eeeee eeee M-eeeeeeeeeeee ee e eeeeeeeeeeee eeeeee ee e “eeee-eeeeeeeeeeee” eeeeee, eeeeee eeeeeeeeeeeeeeeee eeee eee eee eeeeeeeeeee eeeeeeee ee eee eeeeeeee eeee.[‌888‌,‌888‌] Meee M-eeeeeeeeeeee, eeeeeeeee ee eeeeeeeee “eeee-eeeeeeeeeeee” eeeeeeee, eeeeee ee e eeeeeee eeeeee eee eeee ee eee eeeeeeeee-8-ee eeeeee, eee eeee eeeeeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Mee-8-eeeeee-8,8-eeeeeeeeeeeeeeeee-8-eeeeeeeeeeee (‌888‌):[‌888‌]

M eeee ee 8-(eeeeeeeeeeeee)-8-eeeeeeeeeeeeeee-8(8M)-eee (‌888‌; 8.88 e, 88.8 eeee) ee MMM (88 eM) eee eeeeee eeee eeeeeeeee MeM8 (88.8 e, 888 eeee) ee ee eee 88 e. Mee eeeeeeeeee eee eeeeeeee eeeeeee Meeeee eee eee MeM8 eee eeeeee eeee MMM. Mee eeeeeeee eeeeeeee eee eeeeeee eee eeeeeeeeeeee ee eeee e eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) eee eeeeeeeeeeeeee (eMeMM) ee eeee eeeeee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.

8-(Meeeeeeeeee)-8-eeeeeeeeeeeeeee-8(8M)-eee (‌888‌):[‌888‌]

M eeeeeee ee 8-(eeeeeeeeeeeee)-8-eeeeeeeeeeeeeee-8(8M)-eee (‌888‌; 8.8 e, 88.8 eeee), MMe8 (8.88 e, 88.8 eeee), eee Me8M (8.88 e, 88.8 eeee) ee MM8Me8 (88 eM) eee eeeeeeee eeeee eeeee eee 88 e. Mee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeee eeeeeee eee eeeeeeeeee eeee eeeeeee. Mee eeeee eeee eeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee (MeMM) ee eeee eeeeeeeee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 8e, 888.