68003-58-7Relevant academic research and scientific papers
Stereocontrolled Synthesis of N-Vinyl-, N-(1'-Propenyl)-, and N-Unsubstituted-β-lactams from 2-Aza-1,3-butadienes via the Staudinger Reaction
Georg, Gunda I.,He, Ping,Kant, Joydeep,Wu, Zhi-jun
, p. 5771 - 5778 (2007/10/02)
2-Aza-1,3-butadienes 2 and 5 were synthesized in good yields and on a large scale.Reaction of 2 and 5 with acid chlorides in the presence of triethylamine (Staudinger reaction) resulted in the high-yielding formation of N-vinyl- and N-(1'-propenyl)-β-lact
Silylamines in Organic Synthesis. Reactivity of N,N-Bis(silyl) Enamines toward Electrophiles. A Route to Substituted 2-Aza-1,3-butadienes and Pyridines
Corriu, Robert J. P.,Moreau, Joel J. E.,Pataud-Sat, Magali
, p. 2878 - 2884 (2007/10/02)
N,N-Bis(silyl) enamines appeared to be weak nucleophilic reagents and exhibited a very low reactivity toward electrophiles.However, in the presence of a nucleophilic catalyst, nucleophilic activation of the silicon-nitrogen bond was observed.Under fluoride ion catalysis (TBAF or CsF), N,N-bis(silyl) enamines reacted with carbonyl compounds to give substituted 2-aza-1,3-butadienes.Good yields were obtained in reactions with aromatic aldehydes or ketones.In the case of aliphatic carbonyl compounds, 2-aza 1,3-dienes were only formed in moderate yields.Interestingly, enamidines were easily obtained in high yields upon reactions of dimethylformamide in the presence of MeONa as catalyst.The reaction of aromatic α,β-unsaturated ketones gave 2-aza 1,3,5-trienes, which were not isolated but underwent an intramolecular cycloaddition reaction with regioselective formation of substituted 2,4-diarylpyridines.
A Protodesilylation Route for 2-Aza-1,3-diene Synthesis
Chen, Shyh-Fong,Ho, Eugene,Mariano, Patrick S.
, p. 7013 - 7026 (2007/10/02)
A new methodology for 2-aza-1,3-diene synthesis involving protodesilylation reactions of N-1-triethylsilylallyl-imines and their propargyl analogs is described.Synthetic sequences for the preparation of these allyl and propargyl imines starting with propa
MECHANISTIC AND SYNTHETIC ASPECTS OF 2-AZA-1,3-DIENE PREPARATION THROUGH N-(1-TRIETHYLSILYLALLYL)IMINE PROTODESILYLATION
Chen, Shyh-Fong,Mariano, Patrick S.
, p. 47 - 50 (2007/10/02)
Features of a novel method for preparation of 2-aza-1,3-dienes involving CsF induced protodesilylation of N-(1-triethylsilylallyl)imines is described.
