Science of Synthesis

Smalley, R. K., Science of Synthesis, (2002) 11, 313.

Condensation of an α-dicarbonyl compound (e.g., OHC—CHO) with a isoxazole-4,5-diamine is an obvious route to isoxazolo[4,5-b]pyrazines and has been used on several occasions.[‌152‌–‌154‌] This procedure, however, is limited in scope by the instability of the isoxazolediamines, which are used as their hydrochlorides.

Meeeeeeeeeee, eee eeeeeeee ee eee eeeeeeee eeee,[‌888‌] eee eeeeeeeee ee eeeeeeeee[8,8-e]eeeeeeeeee-8,8(8M,8M)-eeeeee ee eeeeeeeeeeee ee eeeeeee 8-eeeeeeeeeeeeeee-8,8-eeeeeeeeeeeee eeee eeeeeeeee eee eeee ee e eeeeeee eeeeeee ee eeeeeeee, eee eeeeeeeeeee ee eeeee eeeeeee ee eee eeeeeeee eeeeeeeeee.[‌888‌,‌888‌] Mee eeeeeeeeeeeeeeeeeeeeeeee eeeeee, e.e. 888, ee eeee eeeeeeee ee eeeeeee eee eeeeeeeeeee ‌888‌ (M8 = Me; M8 = MM8) ee 888–888°M (‌Meeeee 88‌),[‌888‌] eeeee e Meeeeee eeeeeeeeeee ee eee eeeeeeeeeeeee ‌888‌ (M8 = Me; M8 = M) eeeeeeeee eee eeeeeeeee[8,8-e]eeeeeeeeeeeeeee 888.[‌888‌]

‌Meeeee 88‌ Meeeeeeee Meeeee ee Meeeeeeeeeeeeeeee[‌888‌,‌888‌–‌888‌,‌888‌]

Mee eeeee eeeeeeee ‌888‌ ee eee eeeeeeee eeeeeeeee[8,8-e]eeeeeeeeee eeeeee eeee eeee eeeeeeee ee eee eeeeeeeeeeee ee e 8-eeeee-8-eeeeeeeeeeeeeeee ‌888‌ (M8 = MMe; M8 = MM) eeee eeeeeeeee.[‌888‌] Meeeeeeeeeee, eeeeeeeeee ee eeee eeeeeeeee eeee eeee eeee ee eeeeeee e eeeee ee eeeeeeeeeee. Mee eeeeeee, eeeeeeeeee ee eee 8-eeeee-8-eeeee eeeeeeeee ‌888‌ (M8 = MM8; M8 = MM) eeee eeeeeeeeeeeeeee eeeeeee, ee eeeeee eeee eeeeeeeeeeeeeeee eee eeeeee eeeeeeeee eeeeeeee ee eeeeeeeee eeee eeeeeeeee eeeeeee,[‌888‌] eeeeee eee 8-eeeee eeeeeeeee ‌888‌ (M8 = M). Meeeeeeeee ee eee eeeee eeeeeeeeeee ‌888‌ (M8 = MM8; M8 = MM) ee eee eeeee-eeeeee ‌888‌ (M8 = MM8; M8 = MMMM8) eee eeeeeeeeeee eeeee eee eeee eeeeeeeeee eeeeeee eee eeeeeeeeeeeeeeeeeeee ‌888‌ (M8 = M; M = M).[‌888‌] Meeeeeeee[8,8-e]eeeeeeeeee-8(8M)-eeeeeee ‌888‌ (M8 = M, Me, MM8; M = M) eee eeeeeeee (88–88% eeeee) ee e eeeeeeeeeeeee eeeeee ee eeeeeeee eeeeeeeee-8-eeeeeeeeeeeeeeee ‌888‌ (M8 = MM8; M8 = MMMM8) eeee ee eeeeeeeeee ee eeee e eeeeeee ee eeeeeeeeeeeeeee eeee eee eee eeeeeeeee.[‌888‌] Meeeee ee 8-eeeeeeeeeee eeeeeeeee[8,8-e]eeeeeeeeeeeee, eeeeeeee ee eeeeeeeeeee ee eeeee-eeeeee ‌888‌ (M8 = MMMMM; M8 = MM) eeee ee eeee eeeeee eee eeeeeeee (88–88%) eee eeeeee ee eee eeeeeeee eeeeeeeeeee, eee eeee ee eeeeeee, eee eee eeeeee ee eee eeee eeeeee.[‌888‌]

8-Meeeeeeeeeeeee-8-eeeeeeeeeeee ‌888‌ (M = M), e eeeeee eeeeeeeee ee eeeeeeeee[8,8-e]eeeeeeeee (eee Meeeeee ‌88.88.8.8.8.8‌), ee eeee e eeeeee eeeeeee eee eeeeeeeee[8,8-e]eeeeeeeeeee. Meeeeeeeeeee ee eee eeeee eeeeeeee eeee eeeeeeeeeeeeeee ee eee eeeeeeee ee eeee eeeeeeeee eee 8-eeeeee eeeeeeeeee 888,[‌888‌] eeeeeee eeeeeeeeeee ee eee eeeeeeeee ee ee eeeee ee eeee eeeeeeeeeee ee eeee eeeeeeeee[‌888‌] eeeee ee eeeeeeeee ee eee 8-eeeeeeeeeee 8-eeeeee eeeeeeeeeee 888. Me eeeeeeee, eeeeeee eeeeeeeeeeeeeeee eeeeeee eeee eeeeeee ee eee eeeeeeee ‌888‌ (M = MMM) ee 8-eeeeeeeeeeeeeee[8,8-e]eeeeeeeeee 8-eeeee ‌888‌ ee eeeeeeee eeeee (88%).[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeee[8,8-e]eeeeeeeee-8-eeeee (888, M8 = M; M8 = Me):[‌888‌]

M eeee ee eee eeeeeeeeeeeeeeeeeeeeeeeeee ‌888‌ (M8 = MM8; M8 = MM; M8 = Me; 88 e, 8.888 eee) ee ee eeeeeeeee eeeeeee ee Me8M (88 eM) eee MM(MMe)8 (88 eM) eee eeeeee eeeee eeeeee eee 8 e. Mee eeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeee eee eeeeee eeee eeeeeeeee MM8 (888 eM), eeeeeeeee eeeeeeeee eeeeeeeeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eee 8 e ee ee, eeee eeeeeeeeeeee, eee eee eeeeeee eeeeeee ee eeeeeeeeee. Mee eeeeeee eee eeeeee eeee M8M eee eeeeee eeeee ee eeee 8.8 e ee eeeeeeeee eeeee. Me eeeeeeeeee 8.8 e ee eeeeeee eeeeeeeee eeee eee eeeeeeee ee eeeeeeee; eeeee eeeee: 8.8 e (88%); ee 888–888°M (ee MeMM ee MMM/MeMM).

8-Meeeeeeeeeeeeee[8,8-e]eeeeeeeeee 8-Meeee (888):[‌888‌]

M eeeeeee ee eeeee ‌888‌ (M = MMM; 8 e, 8.88 eee) eee MM(MMe)8 (88 eM) eee eeeeee eeeee eeeeee eee 8 e. Mee eeeeeeeee MeMM eee eeeeee MM(MMe)8 eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeeee eeeeeee eeeeeeeeeeee (MeMM); eeeee: 8.88 e (88%); ee 888–888°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e, 888.