Aminoacetaldehyde diethyl acetal

C11H9I3N2O4 117-96-4) see Metrizoic acid aminoacetaldehyde diethyl acetal (C H 5N02 645-36-3) see Thiamazole p-aminoacetanilide... 

Aminoacetaldehyde diethyl acetal, d306 Aminoacetaldehyde dimethyl acetal, d506 1-Aminoadamantane, a64 Aminoanisoles, m48 thru m50 / -Aminoazobenzene, p88... 

Allyl sulfide, d27 Aluminon, a316 A-Amidinosarcosine, c277 Aminoacetaldehyde diethyl acetal, d254... 

The parent compound of this series, pyrazine, was first prepared in trace amounts by Wolff (30) by heating aminoacetaldehyde diethyl acetal [H2NCH2CH(OEt)2] with anhydrous oxalic acid at 110-190°C, and later in better yield by heating the mercuric or platinic chloride double salts (of the aminoacetaldehyde acetal) with hydrochloric acid (31) it was also obtained from aminoacetaldehyde with mercuric chloride in sodium hydroxide (23). Wolff in 1893 (22) also prepared pyrazine by decarboxylation of the tetracarboxylic acid, obtained by oxidation of tetramethyl-pyrazine and Stoehr (32) prepared it by the distillation of piperazine with lime and zinc dust. Brandes and Stoehr (33) in 1896 described the preparation of pyrazine by heating glucose with 25% aqueous ammonia at 100°C. 

Diketopiperazines and benzodiazepin-2,5-diones represent the same target obtained by performing a Ugi MCR on the universal Rink-isonitrile resin [347]. The final product could be cleaved from the resin with HOAc/1,2 dichloroethane 1 9 (v/v). Wang resin-bound isonitrile (419) has been employed in a Ugi MCR-N-acyli-minium ion cyclization [348]. Using aminoacetaldehyde diethyl acetal (420) and then exposing the Ugi products to a 20% dichloromethane solution of TFA, the desired A -2-oxopiperazines (422) were obtained with simultaneous release from the resin (Scheme 86). 

The nucleophilic substitution of 4-chloro-5-nitropyrimidines by a-aminocarbonyl compounds, followed by cyclization and oxidation, is also a useful, and widely applicable, method for the synthesis of pteridines (in place of the 5-nitro substituent aryldiazenyl or nitroso moieties can also be used). This reaction is sometimes known as the Polonovski-Boon synthesis.130,131 The use of aminoacetaldehyde diethyl acetal gives 6,7-unsubstituted pteridines, whilst amino ketones, aminonitriles, and amino esters give 6-alkyl-, 6-amino-, and 6-oxopteridines, respectively. 

Aminoacetaldehyde diethyl acetal was obtained in 74% yield by heating a methanolic solution of chloroacetaldehyde diethyl acetal with 18 equivalents of anhydrous ammonia in a pressure vessel at 140° for 10 h.505 2-Amino- and 2-(methylamino)-propionaldehyde diethyl acetal were prepared in 55 %and 40 % yield, respectively, under similar conditions.506 Aromatic amines are best brought to this reaction as A-metal derivatives. 

The Pictet-Spengler reaction has been combined with Ugi multi-component chemistry to construct a number of polycyclic indoles. Isonitrile derivatives prepared from tryptamine (or methyl tryptophanate), a carboxylic acid and formaldehyde condense with aminoacetaldehyde diethyl acetal. A few examples employed substituted aldehydes [352]. 

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