Synthesis of α-amino amides via α-amino imidoylbenzotriazoles

Abstract

Reactions of isonitriles 11a-c with N-(?-aminoalkyl)benzotriazoles 10a-k afford N-(?-aminoimidoyl)benzotriazoles 12a-q which on hydrolysis by dilute hydrochloric acid gave ?-amino amides 14a-j.

Hindered Rotation in Some Organic Dithiocarbamates

“…Such an effect has also been observed for G = when Me is replaced by iPr or iBu with slight difference for formamides (Me 2 NCHO: 87.5, iPr 2 NCHO: 86.1) 23-29 and more strongly for acetamides (Me 2 N-CO-CH 3 : 72.7, iPr 2 N-CO-CH 3 : 67.7) 23,26,29,30 or dithiocarbamates (Me 2 N-CS-SMe: 66.5 ± 2, iBu 2 N-CS-SMe: 63.7 ± 0.02). 4a, 8,39,40 Interestingly, Table 2 shows also that the free energies of activation in the range 58-70 kJmol −1 obtained for the dithiocarbamates 1-5 are nearly similar to or slightly higher than those reported for carbamates, 41 but lower than that in structurally related thioamides, which is in fair agreement with the results already reported by Kalikhman et al for dithiocarbamate 1 and its derivatives. 40 The 1 H NMR spectrum of 5 in CDCl 3 , at 50 • C, shows two signals at 3.77 and 4.15 ppm with an integration of 4H for each, corresponding to O(CH 2 ) 2 and N(CH 2 ) 2 , respectively ( Table 2).…”

Solid phase synthesis of TyrT, a thymine–tyrosine conjugate with poly(A) RNA-binding ability

“…In this regard, it is worth to outline the importance of amino amides, molecules of remarkable biomedical signicance as seen in case of numerous anti-inammatory, antibacterial, analgesic and anaesthetic drugs. 15 CD poly(A) RNA-binding studies First the CD prole of TyrT was analysed at pH 7.5 and 10 C. Fig. 4 shows the CD spectrum of TyrT (…”

Capture of benzotriazole-based Mannich electrophiles by CH-acidic compounds

“…A significant diversification is exemplified by the development of mild benzotriazole-mediated aminoalkylations and related reactions. [12][13][14][15] Benzotriazole-based aminoalkylating reagents have been readily utilized with various nucleophiles, including: enolates, 16 imidazolidine derivatives, 17 isonitriles, 18 enol ethers, [19][20][21][22] enamines, 20,22,23 and enamides. 22,23 Many active pharmaceutical ingredients (APIs) are obtained through a key Mannich step or display the typical core of a Mannich base.…”