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15.1.1.1.7.3.5.2 Variation 2: From Functionalized Enamines and α,β-Unsaturated Carbonyl Compounds

DOI: 10.1055/sos-SD-015-00002

Spitzner, D.Science of Synthesis, (20051569.

Propenal reacts with 3-aminobut-2-enoates (3-aminocrotonates) 236 to give 1,4-dihydropyridines which are oxidized in one pot with nitric acid, manganese(IV) oxide, or sulfur to provide pyridines 237 (Scheme 79).[‌292‌‌294‌]

Meee-eeeeeeeee eeeeeeeeeeee ee ee eeeeeee, e.e. 88, eeee ee α,β-eeeeeeeeeee eeeeeeee ee α,β-eeeeeeeeeee eeeeee, e.e. 888, eeeee eee eeeeeeeeeeee eeeeeeeeeeeeeee eeeee ee eee eeeeeeee, eee eeeeeeee eeeee eeee eeeeeeeee eee eeeeeeee ee eeee eee eeeeeeee, e.e. 888 (Meeeee 88).[‌888‌] Mee α,β-eeeeeeeeeee eeeeee eee ee eeeeeeee ee eee eeeeeeeeeeeee eeeeee. Mee eeeeeeeeeeeeeeeee ee ee α,β-eeeeeeeeeee eeeeee eeee e 8-eeeeeeee-8-eeeeee eeeee eeeeeeee ee 8,8-eeeeeeeeeeeeeeee; eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee eee ee eeeeeeeeeee eeeee eeeeeeeee eeeeeeeeee (MeMM, Meeeee eeeeee, 8.8eee).[‌888‌]

Mee MMM eeee ee eeeeeee e 8-eeeeeeee-8-eeeee eeee eeeeeeeeee (eeeeeee, eeeee, ee eeeee) eee eeee eeeeeeeeeeee eeeeeeee eeeee eeeeeeeee, e.e. 888 eee 888 (Meeeee 88), ee eee MMM eeeeeeeee eeeeeeee e eeeeeee eeeee ee eee β-eeeeee, e.e. eeee,[‌888‌] eeeeee,[‌888‌‌888‌] ee 8-eeeeeeee (eee 8-eeeeeeee eeeeeeee 888 eee eeeeeeee eeeeeee eeeeeeeee eee eeee ee eeeee eeeeeeee ee eee eeeeeeeeeeee eeee eee eeeeeee).[‌888‌,‌888‌]

Meeeee 88 Meeeeeee ee Meeeeeeeeeeeee Meeeeeee eeee α,β-Meeeeeeeeee Meeeeeee Meeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌]

Meeeeeeee eeeeeeeeeeeeeeeeeee eeeee eeeeeeeee eeee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeee eeee eeeeee eeeeeeeeeee eeeeeeeee, e.e. 888 (Meeeee 88). Meee eeeee ee ee e eeeeee eee eeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeee. Mee eee eeee ee eeeee ee eee eeeeeeeeeeeeee Meeeeee eeeeeeee ee eee eeeeeeeee eeeeeeeeeeeeeeeeee ee eee eeeeeeeeeee eeeeeeee eeeeeeee. Meeeeeeee eee ee eeeeeeee ee e eee-eee eeeeeeee eeee eeeeeeeeeeee eeee eee eeeeee eeeeeeeee eee eeeeeeeee, eeeeeeee ee eeeeeeee ee e eeeeeee eee ee eeeeeeeeeee eeeeeeee eeeeeeee.[‌888‌] Meee, eee eeeeeeeeeeeeeeeeeee, e.e. 888, eee ee eeeeeeee ee eee eee eeee eeeeeeeee eeeeeee eeeeeeeeeeeeeeeeee eee eeeeeeee eee eeeeeee ee eee eeee eee eeee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee (MMM + MM + M eeeeeee, eee Meeeeee 88.8.8.8.8.8.8).

Meeeeeeeeeee Meeeeeeee

Meeee 8-Meeeeeeeeeeeee-8-eeeeeeeeeee (888, M8=Me):[‌888‌]

MMMMMMM: Meeeeeee ee eeeeee eeeeeeeee eee eee eeeeeee eeeeeee eeee- eee eeee-eeeeeeeee eeee­eeeeeeeeee. Me ee eeeeeeeeee ee eee eeeeeee eee e eeeeee eeeeeeeeeee.

Me e eeeeeee eeeeeee ee eeeee (8M)-8-eeeeeeee-8-eeeeee (88.8e, 8.88eee), eMeMM (888eM), eee eeeeeeeeee (8eM) ee 88°M eee eeeee eeeeeeee (88eM, 8.88eee) eeeeee 8e. Mee eeeeeee eee eeeeeeee eee 8.8e, eeeeee, e eeeeee eeeeeee ee eeeeeeee (88eM, 8.88eee) eee eeeee, eee eee eeeeeee eee eeeeeeee eee ee eeeeeeeeee 8.8e. Mee eeeeeee eee eeeeeee ee eeeeeeeeeeee eee eee eeeeeee, eeeeee ee 888°M, eee eeeeeee eeee eeeeeeee eeeeee (88.8e, 8.88eee) eeeee ee eeeee eeeeeeee [MMMMMMM: Meeeeeee eeeeeee (M8M) ee eeeeeeee ee eeee eeeeeeee. Mee eeeeeeeeee eeeeee ee eeeeeeeee ee e eeee-eeeeeeeeee eeee eeee]. Mee eeeeeee eee eeeeee eee ee eeeeeeeeee 8e ee 888°M eee eeeeeee ee 888°M eee 8.8e. MMMe8 eee eeeee ee eee eeeeee eeeeeee, eee eeeeee eee eeeeeee, eee eee eeeeeeee eee eeeeeeeee eeee 8M MMe (8×888eM). Mee eeeeeee eeeee eee eeee eeeee eeee 8M MeMM, eeeeeeeee eeee MMMe8 (8×888eM), eee eeeeeee eeeeee eeee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 88.8e (88%); ee 888°M/8.8eMe.

Meeee 8-Meeeee-8-(eeeeeeeeeeeeeee)eeeeeeee-8-eeeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee eeee ee eee α,β-eeeeeeeeeee eeeeeeeeeeeeeee eeeeee 888 (8eeee) eee eeeee (8M)-8-eeeeeeee-8-eeeeee (88; 8eeee) ee MeMM (8eM) eee eeeeeeee eee 88e. MMMe8/eeeeeeee/eeeeee eee (8.8e) eee eeeee eee eee eeeeeee eee eeeeeeee eee e eeeeeee 88e. MeM8 (8.8e, 88eeee) eee eeee eeeee eee eee eeeeeee eee eeeeeeee eee ee eeeeeeeeee 88e. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeeee [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee) ee eeeeee/MeMMe 8:8].

8,8-Meeeeeee-8-(8-eeeee)eeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeeeeeeeeeeeeee 888 (8.88e, 8eeee) ee MMM (88eM) eee eeeee ee MeMe (8eeee) ee MMM (88eM) ee 8°M eeeee M8. Mee eeeeeee eee eeeeee ee ee, e eeee ee 8-eeeeee-8-(8-eeeee)eeee-8-eeeee (8.88e, 8eeee) ee MMM (88eM) eee eeeee, eee eee eeeeeee eee eeeeeee eee ee. 88e. Mee eeeeeee eee eeeeeee eeee M8M (88eM) eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeeee eeee eeeeee eeee M8M, eeeee (MeMM8), eee eeeeeeeeeeee ee eeee e eeeee eeeeeee eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee eeeeeee, eeeeee); eeeee: 8.88e (88%).

References