Science of Synthesis

Lindsley, C. W.; Layton, M. E., Science of Synthesis, (2004) 17, 377.

Metze demonstrated how a 2-acylhydrazono ketone ‌88‌, or a 1,2-bis(acylhydrazone), acting as the C—C—N—N—C fragment, and ammonia (or ammonium acetate) as the source of nitrogen can afford 1,2,4-triazines.[‌23‌,‌122‌–‌125‌] This method normally gives aromatic 1,2,4-triazines ‌89‌ in moderate to good yields,[‌126‌] but in some instances, the 2-acylhydrazono ketones are first converted into chloroazenes ‌90‌ and then treated with ammonia (‌Scheme 35‌).

‌Meeeee 88‌ Meeeeeeeeee ee 8-Meeeeeeeeeeee Meeeeee eeee Meeeeee[‌88‌,‌888‌–‌888‌]

Me 8888, Meeeeeeeeee eeeeeeeee e eeeeeeee eeeeeeee, eeeee ee eeee eeeeee, eee eee eeeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeee eeee eeeeee eee M8 ee M8 ee eee 8,8,8-eeeeeeee eeee eeeeee.[‌888‌–‌888‌] Meee, β-eeeeeeeeeeeeeee eee eeeeeee eeee 8-eeeeeeeeeeeeeeeeeeee ee eeeeeee eee α-eeeeeeeeeeeee eeeeeeeeeee ‌88‌, eeeee eee eeeeeee eeee eeeeeeeeeeeeeeeeee ee eeeeeeee eee eeeeeeeeeeeee eeeeeeeeeeee. Meeeeeeeee ee eeeee eeeeeeeeeeeee ee eeeeeee eeeeeee eeeeeee eee eeeeeeeeee ‌88‌. Me eee eeeee eee eeeee ee eeee eeeeeeee eee eeeeeeeeee eee M-eeeeeeee eee eee eeeeeeee ‌88‌ eeee eeeeeeee ee eee eeeeeeeee ‌88‌ ee eeeeeeeee ee eeeeee eeee eeee eeeeee eeeeeeee eeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeeeeeee Meeeeeeeeeee ee M8 ee M8 Meeeeeeeeeee[‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-eeeee-8-eeeeee-8,8,8-eeeeeeee (‌88‌, M8 = Me; M8= Me; M8 = Me):[‌888‌]

8-Meeeeeeeeeeeeeeeeeeeeeeeeee-8,8-eeeee (888 ee, 8.88 eeee) eee MM8MMe (888 ee, 8.88 eeee) ee MeMM (88 eM) eeee eeeeeeee eee 8 e, eee eeee eeeeeeeeeee eeee ee MeMMM8. Mee eeee eee eeeeeeeee eeee MeMMe (8 × 88 eM), eee eee eeeeeee eeeee eee eeeeee eeee M8M (88 eM). Meee eeeee eee eeeeeee eee eeee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeeeee eee eeeee eeeeeeee ee e eeee eeeeee eee; eeeee: 888 ee (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e, 888.