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1.2.1.4.4.2 Solvent-Free Betti Reaction

DOI: 10.1055/sos-SD-210-00078

Bernardi, L.; Ricci, A.Science of Synthesis: Multicomponent Reactions, (20141157.

The prolonged reaction times and the requirement of anhydrous alcoholic ammonia solutions in Betti reactions can be overcome by using solid ammonium acetate as a source of ammonia. By heating at 60 °C without solvent, the oxazine products 32, which can be carried on to the Betti base hydrochlorides by acidic hydrolysis, can be obtained quickly and in very good yields (Scheme 36).[‌54‌]

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Meeeeeeeeee 88

Me8 Meee (eee) Meeeee (%) Mee
Me 88 88 [‌88‌]
8-MMM8M8 88 88 [‌88‌]
8,8-Me8M8M8 88 88 [‌88‌]
8,8,8-(MeM)8M8M8 88 88 [‌88‌]
8-MeMM8M8 88 88 [‌88‌]
8-MM-8-MeM8M8 88 88 [‌88‌]
8-eeeeeee 88 88 [‌88‌]
8-eeeeeee 88 88 [‌88‌]

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M eeeeeee-eeee eeeeeeee eee eeee ee eeeeeeee eeee (M)-8-eeeeeeeeeeeeeeee (Meeeee 88).[‌88‌] Mee eeee 8-eeeeeeee eee eeee 8-eeeeeeee eee eeeeeeee-8-ee eeeeeeee eeee eee eeeeeeeeeeeee Meeee eeeee 88. Meee eeee eeeeeeee eeeee, eee eeeeeee ee eee eeeeee ee eeeeeeeeeee eeeeeee.

Meeeee 88 Meeeeee-Meee Meeee Meeeeeee eeee (M)-8-Meeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 Meee (e) eee (%) Meeeee (%) Mee
Me M M (MMMM)8 8 88:8 88 [‌88‌]
8-Mee M M (MMMM)8 8 88:8 88 [‌88‌]
8-MeM8M8 M M (MMMM)8 8 8.8:8 88 [‌88‌]
8-eeeeeeee M M (MMMM)8 88 8.8:8 88 [‌88‌]
Me M M (MMMM)8 88 88:8 88 [‌88‌]
eMe M M (MMMM)8 88 88:8 88 [‌88‌]
Me (MMMM)8 M M 8 8.8:8 88 [‌88‌]
Me MMMMMMM M M 88 8.8:8 88 [‌88‌]

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Meeeee 88 Meeeeee-Meee Meeee Meeeeeee eeee (M)-M-Meeeee-8-eeeeeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeee 88

Me8 Meee (°M) Meee (e) eee Meeeee (%) Mee
Me 88 88 >88:8 88 [‌88‌]
8-eeeeeeee 88 88 >88.8:8.8 88 [‌88‌]

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8,8-Meeeee-8,8-eeeeeee-8M-eeeeeee[8,8-e][8,8]eeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eee eeeeeeee (8.8 eeee), 8-eeeeeeee (888 ee, 8.8 eeee), eee MM8MMe (888 ee, 8.8 eeee) eee eeeeee ee e eeeee-eeeeeeee eeeee ee 88 °M. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM. Meeee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeee ee ee eee eeeeee eeee eeeeeee eee. Mee eeeeeeee eeeee eee eeeeeeeee ee eeeeeeeeee, eeeee, eee eeeeeeeeeeeeee (MeMM).

8-[(M)-Meeeee{[(8M)-8-eeeeeeeeeee]eeeee}eeeeee]eeeeeeeeee-8-ee [88, M8 = Me; M8 = M8 = M; M8,M8 = (MMMM)8]; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8-eeeeeeee (8.88 e, 8.8 eeee), MeMMM (8.88 e, 8.88 eeee), eee (M)-8-eeeeeeeeeeeeeeee (8.88 e, 8.88 eeee) eee eeeeeee ee 88 °M eee 8 e eeeee M8. Me eeeeeeeee eee eeeeeeee ee eee eeeeeeee ee MMM eee 8M MMM, ee eee eeee eeee eee eeeeeeeee ee eee eeeeeee eeeeee eeeeee eee eeeee 8 e eee eee eeeeeee ee (8.8:8 ee 8 e) eeeeeeeee eeee eeee (88:8 ee 8 e) eeee eee eeeeeeeee ee e eeeee eee eeeeeeeeeee eeeeeee. Mee eeeeeee eee eeee eeeeeeeee ee ee eeee MeMM (8 eM). Mee eeeee eeeeeeee eeee eeeeeeeee, eeeeee eeee MeMM (8 × 8 eM), eee eeeeeeee ee eeeeeeeeeeeeeee (MeMMe/eeeeee) ee eeee eee eeee eeeeeee; eeeee: 8.88 e (88%); ee 88:8. Mee eeeee eeeeeeee 88 eeee eeeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee) eeee eee eeeeeee.

8-[(M)-{Meeeee[(8M)-8-eeeeeeeeeee]eeeee}(eeeeee)eeeeee]eeeeeeeeee-8-ee (88, Me8 = Me); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee MeMMM (8.8 eM, 88 eeee), (M)-M-eeeeee-8-eeeeeeeeeeeeeeee (8.88 e, 88 eeee), eee 8-eeeeeeee (8.88 e, 88 eeee) eee eeeeeee ee 88 °M eee 88 e. MeMM (8 eM) eee eeeee eee eee eeeeeeeeeeee eeeeeee eee eeeeeeeee eee eeeeee eeee MeMM (8 eM) ee eeee eee eeeeeee ee eeeee eeeeeeee; eeeee 8.88 e (88%); ee >88:8.

References


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