Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate in the synthesis of heterocyclic systems. An attempt to prepare benzoylamino substituted azolo‐ and azinopyrimidines with a bridgehead nitrogen atom

1,2,4-Triazolo[1,5-a]pyrimidines

Abstract: Publisher Summary The formation of 1,2,4-triazolo [1,5-a] pyrimidines (TPs) was first reported by Biilow and Haas Over the next 50 years, only a few papers and patents on TPs were published, which were included in Mosby's comprehensive monograph on “Heterocyclic Systems with Bridgehead Nitrogen Atoms” Most syntheses of TPs start either from a 1,2,4-triazole derivative or from a pyrimidine residue and need annulation of a second heterocyclic ring Preferably 5-amino-1,2,4-triazoles (AT) and 2-hydrazinopyrimidines (HP) are used as starting synthons In the synthesis of TPs from HPs, intermediates are believed to exist and have been isolated in many cases These products and other acylated HPs may serve as convenient starting materials for cyclization reactions Acylated HPs are also prepared from 2-alkylthiopyrimidines and acylhydrazines and, further, cyclized in situ to triazolopyrimidines Many TPs have been tested as potential growth inhibitors of microorganisms, because they are isomeric to purines and in some cases can be converted to nucleoside analogs

The synthesis and transformations of ethyl (Z)-2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-dimethylaminopropenoate, a new reagent in the synthesis of heterocyclic compounds

Abstract: Ethyl (Z)-2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-dimethylaminopropenoate (5), a new reagent in the synthesis of heteroaryl substituted β-amino- α,β- -dehydro—amino acid derivatives and some fused hetero-cyclic systems, was prepared from ethyl N-2,2-bis(ethoxycarbonyl)vinylglycinate (3) and N,N-dimethyl-formamide dimethyl acetal (4). The substitution of the dimethylamino group in the compound 5 with heterocyclic amines produced ethyl 2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-heteroarylaminopropenoates 7a-f and, in some instances, [2,2-bis-(ethoxycarbonyl)vinyl]aminoazolo- or -azinopyrimidine derivatives 8g-k.

Methyl 2-benzoylamino-3-dimethylaminopropenoate in the synthesis of heterocyclic systems. The synthesis of benzoyl- amino substituted 7H-pyrano[2,3-d]pyrimidine, 1H,6H-pyrano- [2,3-c]pyrazole and 2H-1-benzopyran derivatives†

Abstract: Methyl 2-benzoylamino-3-dimethylaminopropenoate (6) reacts with heterocyclic compounds containing an active methylene group or potential methylene group in the ring system, such as barbituric acid derivatives 1 and 2, pyrazolones 3 and 4, and resorcinol, in acetic acid to afford the corresponding benzoylamino substituted pyranopyrimidinones 7 and 8, pyranopyrazolones 9 and 10, and 2H-1-benzopyranone 11. The method represents a novel procedure for the preparation of condensed pyranones.

Transformations of N‐heteroarylformamidines into derivatives of β‐heteroarylamino‐α,β‐dehydro‐α‐amino acids, β‐heteroarylamino‐α‐amino acids, and dipeptides

Abstract: Transformations of N'-heteroaryl-N,N-dimethylformamidines 1 as a general method for the preparation of β-heteroarylamino-α,β-dehydro-α-amino acids, β-heteroarylamino-α-amino acid derivatives 5–9, and dipeptides 10, are described.

The synthesis of β‐heteroarylamino‐α,β‐dehydro‐α‐amino acid and β‐heteroarylamino‐α‐amino acid derivatives

Abstract: From heteroarylaminomethyleneoxazolones 4, obtained from N-heteroarylformamidines 2 and 2-phenyl-5-oxo-4,5-dihydro-1,3-oxazole (3), the following β-heteroarylamino-α,β-dehydro-α-amino acid derivatives were prepared: methyl 8 and ethyl esters 9, amides 10 and 11, hydrazides 12, and azides 15. By catalytic hydrogenation the compounds 4 were converted into β-heteroarylamino substituted amides 18 and β-heteroarylamino-α-amino acids 20.

A Simple One-Step Synthesis of Substituted Methyl 2-Benzoylamino-3-arylaminopropenoates, Intermediates in the Preparation of Substituted Arylaminoalanines

Abstract: A simple one-step synthesis of substituted methyl 2-benzolamino-3-anilinopropenoates 8a-r from substituted anilines 7a-r and methyl 2-benzoylamino-3-dimethylaminopropenoates 6 is described. Eine einfache, einstufige Synthese substituierter 2-Benzoylamino-3-arylaminopropensauremethylester, Zwischenprodukte fur die Herstellung substituierter Arylaminoaniline. Eine einfache, einstufige Synthese der substituierten 2-Benzoylamino-3-arylaminopropensauremethylester 8a-r aus den substituierten Anilin-Derivaten 7a-r und 2-Benzoylamino-3-dimethylaminopropensauremethylester 6 wird beschrieben.