Synthesis and characterization of new 2-(alkylamino)acetamides

Abstract

Seven new 2-(alkylamino)acetamides have been synthesized and characterized by 1 H, 13C NMR, NOESY experiments, infrared and mass spectrometry. The structure of 2-(diphenylmethylamino)acetamide 3b was further established by a single crystal x-ray diffraction study. The NMR study of the transformation of several 2-(alkylamino)acetamides to their corresponding morpholin-2-ones shows that these species are thermodynamically favored through preferred conformations as determined by theoretical calculations of 3h.

Oxidation of the Antiviral Drug Acyclovir and Its Biodegradation Product Carboxy-acyclovir with Ozone: Kinetics and Identification of Oxidation Products

“…In accordance with results from HR-MS, the NMR spectra of OP273 revealed that the side chain attached to the guanine moiety remained unchanged as the broad shift at 12–14 ppm, characteristic for the presence of a carboxylic moiety, and chemical shifts of two CH 2 groups (C-10 and C-11) were still present (Figure ). However, in contrast to carboxy-ACV, chemical shifts of protons attached to C-10 at 4.9 and 5.2 ppm in OP273 differ quite substantially, indicating a hindered rotation . The same is true for protons at 7.2 and 7.3 ppm in the 1 H NMR spectrum of OP273 which were assigned to the formamido N-7 (see also the 1 H, 15 N-HSQC spectrum; Figure ).…”

“…However, in contrast to carboxy-ACV, chemical shifts of protons attached to C-10 at 4.9 and 5.2 ppm in OP273 differ quite substantially, indicating a hindered rotation. 44 The same is true for protons at 7.2 and 7.3 ppm in the 1 H NMR spectrum of OP273 which were assigned to the ). The total test duration was 336 h (14 days).…”

Synthesis of α-amino amides via α-amino imidoylbenzotriazoles

“…1 a-Amino amides have been claimed as antiinflammatory, 2 antibacterial, 3 anticonvulsant, 4 and cerebro-protective 5 agents, and utilized as local anesthetics, 6 analgesics, 7 and melanocortin agonists. 8 Available methods for the synthesis of a-amino amides 1 include (Scheme 1): (i) hydrolysis of a-amino nitriles 2; 9,10 (ii) multicomponent Ugi reactions (the four-component variant is shown); 11 reactions of amines with (iii) benzotriazol-l-yl a-amino esters 3 (Y = -OBt) 12 or a-aminoacyl benzotriazoles 3 (Y = Bt), 13,14 (iv) mixed anhydrides 4, 15,16 (v) a-bromo amides 5, 17,18 or (vi) aziridinones 6; 19 (vii) reactions of dichloroacetamide 7 with amines and benzotriazole followed by nucleophilic substitution of benzotriazolyl group in 8; 20 reactions of dimethylcarbamoylsilane 9 with (viii) iminium salts, 21 or (ix) with imines in the presence of boron trifluoride etherate; 22 and (x) Pd-catalyzed double carbohydroamination of iodoarenes. 23,24 Benzotriazole is a versatile synthetic auxiliary for organic synthesis 25,26 and imidoylbenzotriazoles are synthetically useful stable alternatives to the corresponding imidoyl chlorides.…”

Novel hydrido-ruthenium(ii) complexes with histidine derivatives and their application in the hydrogenation of ketones

“…43 Esterification of the latter using thionyl chloride in methanol gave the 1-Me-(S)-histidine-Me-ester. 44 Its ruthenium complex 5 was finally prepared in a one-pot reaction from RuCl 2 (PPh 3 ) 2 in the same way as complexes 1-4 (vide supra).…”

“…43 The 1-methyl-(S)-histidine methyl ester dihydrochloride has been prepared by esterification of 1-methyl-(S)-histidine dihydrochloride according to the general procedure described by Mancilla et al for esterification of a-amino acid. 44 RuCl 2 (PPh 3 ) 3 was prepared by a slight modification of the published procedure. 55 All other reagents used in the experiments were obtained from commercial sources and used as received.…”