The α‐Addition of Immonium Ions and Anions to Isonitriles Accompanied by Secondary Reactions

Abstract

The a-addition of immonium ions and anions (OH-, SeH-, S2O32-, N3-NCO-, NCS-, R-COz-, RO-COz-) to isonitriles, accompanied by secondary reactions, provides a means for the one-stage synthesis of organic nitrogen compounds starting with two to five diferent components. Thus, by the condensations of amines (ammonia, primary, and secondary aliphatic and aromatic amines, hydrazines) and aldehydes or ketones with isonitriles and acids, a number of a-aminocarboxylic acid amides, thioamides, selenoamides, 1,j-disubstituted tetrazoles, hydantoin imides, thiohydantoin imides, a-acylamino carboxylic acid amides, oiigopeptide derivatives, /3--lactams, derivatives of penicillanic acid, urethanes, diacylimides, and various hydrazine derivatives, can be prepared. The reactions are easily carried out and take place under mild conditions. Yields of more than 90 % are frequently encountered.

Prebiotic chemistry: a new modus operandi

“…R f : 0.5 (cyclohexane : EtOAc 4 : 1). 1 (ii) Sodium decyl phosphate Diallyl decyl phosphate (30 mg, 0.10 mmol) was dissolved in CH 2 Cl 2 (5 ml), trimethylsilyl bromide (64 ml, 0.5 mmol) was added and the solution was stirred under a nitrogen atmosphere for 15 h. The reaction mixture was then concentrated in vacuo. The residue was dissolved in H 2 O and the resultant solution was adjusted to pH ¼ 9.0 with 1 M NaOH and lyophilized to give 20 mg (84%) of the title compound as a white semi-solid.…”

“…The residue was dissolved in H 2 O and the resultant solution was adjusted to pH ¼ 9.0 with 1 M NaOH and lyophilized to give 20 mg (84%) of the title compound as a white semi-solid. 1 figure 3). …”

“…1 figure 4). (b) Mixed chain length alkanol phosphorylation Decanol (23.6 ml, 0.12 mmol), hexanol (15.5 ml, 0.12 mmol), ethanol (0.25 ml), ammonium phosphate (14.2 mg, 0.12 mmol) and urea (74 mg, 1.20 mmol) were dissolved in H 2 O (0.5 ml). The solution was applied evenly to two glass fibre discs (25 mm  0.68 mm), the discs were dried at 408C for 2 days and then heated at 1008C for 24 h. The discs were then washed with H 2 O (10 ml) and the washings were lyophilized.…”

“…The lyophilisate was then dissolved in D 2 O (3 ml) and adjusted to pD ¼ 9.0 to give complete solubility. The sample was analysed by 1 …”

PREPARAÇÃO DE Α-Acetiloxi-N-Cicloexilamidas ATRAVÉS DA REAÇÃO DE PASSERINI UTILIZANDO DIMETILCARBONATO COMO SOLVENTE AMBIENTALMENTE AMIGÁVEL

“…Posterior rearranjo no intermediário II leva ao produto da reação. É sabido que a reação de Passerini é acelerada em solventes apróticos, indicando um mecanismo predominantemente não-polar, 29 embora também existam exemplos de reações de Passerini conduzidas em água como solvente. 30 Recentemente, cálculos teóricos demonstraram, entretanto, que um quarto componente ácido pode estar envolvido no estado de transição, facilitando o rearranjo para fornecer o produto final, através de uma reação pseudo-tetracomponente.…”