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2.1.3.2 Reactions with an NH-Acid Component

DOI: 10.1055/sos-SD-211-00020

Shaabani, A.; Sarvary, A.; Shaabani, S.Science of Synthesis: Multicomponent Reactions, (2014264.

The amide group is a suitable agent for the trapping of zwitterionic intermediates generated by the addition of isocyanides to dialkyl acetylenedicarboxylates. Because amides are less nucleophilic than amines, they act as NH-acids in protonation of the zwitterion intermediates. Many NH-acids have been used as zwitterion-trapping agents for the formation of functionalized N-heterocyclic compounds such as functionalized pyrroles 28 and 29,[‌29‌] pyrazoles 30,[‌30‌] dialkyl 5-(alkylamino)-1-aryl-1H-pyrazole-3,4-dicarboxylates (e.g., 31),[‌31‌] pyrazolo[1,2-a][1,2,4]triazoles (e.g., 32),[‌32‌] pyrazolo[1,2-a]pyrazoles (e.g., 33),[‌33‌] dihydropyrimidine-2,4(1H,3H)-diones (e.g., 34),[‌34‌] 3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidines (e.g., 35),[‌35‌] 5H-thiazolo[3,2-a]pyrimidines (e.g., 36),[‌36‌] 4H-pyrido[1,2-a]pyrimidines (e.g., 37),[‌37‌] pyrimido[1,2-a]pyrimidines (e.g., 38), pyrazino[1,2-a]pyrimidines (e.g., 39),[‌38‌] and 5H-imidazo[2,1-b][1,3]oxazines (e.g., 40) (Scheme 9).[‌39‌]

Meeeee 8 Meeeeeeee ee Meeeeeeeeeeeee M-Meeeeeeeeeee Meeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 8

M8 M8 M8 Meeee (%) Mee
e-Me Me MMe 88 [‌88‌]
Me Me Me 88 [‌88‌]

Meeeee eeeeeeeeeee (e.e., 88) eee eeeeeeeeeee eee eeeee-eeeeeeeee eeeeeeeee ee eeeeeeeeeee, eeeeeee eeeeeeeeeeeeeeeeeeeeeee, eee MM-eeeee (Meeeee 88). Meeeeee MM-eeeee eeee eeee eeee ee eeeeeeeeee-eeeeeeee eeeeee, eeee ee eeeeeeeeeee eeeeeeeeeee 88,[‌88‌] eeeee 8-(eeeeeeeee)-8-eeeeeeeeeee (e.e., 88),[‌88‌] M-eeeeeeeeeeeeeeeeeeeeeee (e.e., 88),[‌88‌] eeeeeeeeeeeeeeeee (e.e., 88),[‌88‌] (eeeeeeeeeeeeee)eeeeeeeeee 88,[‌88‌] eeeeeeeeee (e.e., 88),[‌88‌] eeeeeeee-8,8-eeeee (88; eeeeee), eeeeeeeeeee (88), eeeeeeeeeee (88), eeeeeeeeee 88,[‌88‌] eeeeeee-8(8M)-eee (88), eee eeeeeeeeeee-8(8M)-eee (88).[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeee Meeeeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
8,8-Me8M8M8 Me Me 88 [‌88‌]
Me Me M 88 [‌88‌]

Meeeeeeeeee 88M

M8 M8 M8 Meeee (%) Mee
Me MM8 M 88 [‌88‌]
e-Me M Me 88 [‌88‌]

Meeeeeeeeee ee eeeeeeeeeee (88) ee eee eeeeee eeeeee eeeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeee eeeeeeeeeee eee 8,8-eeeeeeeeeee-8-eee-8,8-eeeee eeeee ee eeeeeeeeeeeeee eeeeeee, eeeee eeeeeee eeeeee-eeeeeeee Meeeeee-eeee eeeeeeee ee eee eeeeeeeee eeee ee eee MM-eeee ee eeeeeee eeeeee eeeeeeeeeeeeee eeeeeeeeee eeeeeeeeeee 88; eeeeeee eeeeeee 88 eee eeeeeeeeee ee eeee eeeeeeee. Meee 8-eeeeee-8-eeeeeeeeeeeeee ee eeeeeeeee ee eee MM-eeee eeeee eee eeee eeeeeeeeee, eeee eeeeeeeeee eeeeeeeeeee 88 eee 88, eeeeeeeeeeee, eee eeeeeeee eeee eee eeeeeeee eeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeee eeeeeee Meeeeeeeeee, 8,8-Meeeeeeeeee-8-eee-8,8-eeeee, eee MM-Meeee[‌88‌]

Meeeeeeeeee 88

M8 Meeee (%) Mee
88 88
e-Me 88 88 [‌88‌]
Me 88 88 [‌88‌]

Meeeeeeeeee 88M

M8 Meeee (%) Mee
e-Me 88 [‌88‌]
Me 88 [‌88‌]

Mee eeeeeeeeeeeeee eeeeeeeee ee eeeeee eeeeeeeeeee eeeeeee-8-eee eeeeeeeeeee 88 eee eeeeeeee ee eee eeeeeeee eeeeeeeeeeee eeeeeeeeeeee eeeeeeeee ee eee eeeeeeee ee ee eeeeeeeeee ee eeeeeeee eeeeeeeeeeeeeeeeeeeeee eeee M-eeeeeeeeeee-8-eeeeeeeeeeeeeeeeeeee 88 eee eeee eeeeeeee (Meeeee 88).[‌88‌] Meee eeeeeeeeee eeeeeeeeee ee (eeeeeeeeeeeeee)eeeeee eeeeeeeeee ee eeeeeeee eee eeeeeeeeeeeee eeeeeee-8-eeee 88 eee eeeeeeee, eeeeeee eeee eeee-eeeee eeeeeeeeee, eee eeeeeeeeeeeeee eeeeeeeeeeee eeeeee ee eee eeeeeeeee eeeee ee eee eeeeeeeee eeeeeeeeee eeeeee eeee eee eeeee, eee eeeeeee 88 ee eeeeeeee.

Meeeee 88 Meeeeeee ee Meeeeeeeee, Meeeeeee Meeeeeeeeeeeeeeeeeeeee, eee M-Meeeeeeee-8-eeeeeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 Me8 Meeee (%) Mee
Me Me 88 [‌88‌]
Me 8-MM8M8 88 [‌88‌]
Me 8-MeM8M8 88 [‌88‌]
Me 8-MeM8M8 88 [‌88‌]
Me 8,8-Me8M8M8 88 [‌88‌]
Me 8-M8MM8M8 88 [‌88‌]
Me 8-M8MM8M8 88 [‌88‌]
Me 8,8-(MeM)8M8M8 88 [‌88‌]
MM8MM8Me Me 88 [‌88‌]
MM8MM8Me 8-MeM8M8 88 [‌88‌]
MM8MM8Me 8-MeMM8M8 88 [‌88‌]
MM8MM8Me 8-Mee 88 [‌88‌]
MM8MM8Me 8-M8MM8M8 88 [‌88‌]

Meeeeeeeeee 88M

Me8 Meeee (%) Mee
Me 88 [‌88‌]
8-MM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-MM8M8 88 [‌88‌]
8-M8MM8M8 88 [‌88‌]
8-MeMM8M8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeee eeeee-8,8-Meeeeeee-8-[(8-eeeeeeeeeeeeeee)eeeeeeeee]-8,8-eeeeeeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeee eeee ee 8,8-eeeeeeeeeeee (8.88 e, 8 eeee) eee MMMM (8.888 e, 8 eeee) ee 8 M ee eeeeeee (88 eM), 8-eeeeeeeeeeeeeee eeeeeeeeee (8.888 e, 8 eeee) eee eeeee ee −8 °M eeee 8 eee. Mee eeeeeee eee eeee eeeeeee ee eeee ee ee ee eee eeeee eee 8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeee eeeee eee eeeeeeeeeeeeee (Me8M) ee eeeeee eee eeee eeeeeee ee e eeee eeeeee eeeeee; eeeee: 8.88 e (88%).

Meeeeeee 8-[(eeee-Meeeeeeeee)eeeeeeeee]-8-(8,8-eeeeeeee-8,8-eeeeeeeeeeeeeeeee-8-ee)eeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeeeeeeee eeeeeee eeee ee 8,8-eeeeeeeeeeeeeeeee (88; 8.88 e, 8 eeee) eee MMMM (8.88 e, 8 eeee) ee eeeeeee (8 eM) eee eeeee eeeeeeee e eeee ee eeee-eeeee eeeeeeeeee (8.88 e, 8 eeee) ee eeeeeee (8 eM) ee −8 °M eeee 88 eee. Mee eeeeeee eee eeee eeeeeee ee eeee ee ee ee eee eeeeeee eee 88 e. Mee eeeeeee eee eeeeeee eee MM8Me8 (8 eM) eee eeeee. Mee eeeeeeeee 8,8-eeeeeeeeeeeeeeeee (88) eeeeeeeeeeee eee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeeeeeee (eeeeee/MeMMe 8:8) ee eeee eee eeeeeee ee eeeeeeeee eeeeeeee; eeeee: 8.88 e (88%).

8-[8-Meeeeee-8-(eeee-eeeeeeeeee)-8-eeeeee-8-eeeee]-8,8-eeeeeeeeeeeeee-8(8M)-eee 8,8-Meeeeee (88, M8 = e-Me); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeeeeeeee eeeeeee eeee ee 8,8-eeeeeeeeeee-8-eee-8,8-eeeee (8.88 e, 8 eeee) eee eeeeeeeee (8.88 e, 8 eeee) ee eeeee Me8M (88 eM) eee eeeee e eeeeeee ee eeee-eeeee eeeeeeeeee (8.88 e, 8 eeee) eee eeeee Me8M (8 eM) ee ee. Mee eeeeeee eee eeee eeeeeee eee 88 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee [eeeeee eee (Meeee 888–888 eeee), eeeeee/MeMMe] ee eeeeee eeeeee eeeeeee; eeeee: 8.88 e (88%).

Meeeeeee 8-Meeee-8-(eeeeeeeeeeeeeeee)-8-eeeee-8-eee-8,8,8,8-eeeeeeeeeeeeeeeeee-8,8-eeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eee eeeeeeeeee (8 eeee), MMMM (8 eeee), eee eee M-eeeeeeeeeee-8-eeeeeeeeeeeeeeeeeee 88 (8.8 eeee) eee eeeeeee ee MM8Me8 ee ee. Meeee eeeeeeeeee ee eee eeeeeeee, ee eeeeeeeee ee MMM, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8).

References


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