Tetrazolverbindungen. 1. 1‐Aryl‐5‐(2‐dialkylamino‐vinyl)‐1H‐tetrazole aus 3‐Chlor‐propen‐iminiumsalzen

Fischer, Gerhard W.; Herrmann, Michael

doi:10.1002/prac.19883300617

Cited by 14 publications

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References 15 publications

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“…In der Umsetzung von 3-Chlor-propen-iminiumsalzen 3 mit iibersehussigem Natriumazid wurde kurzlieh [2] ein einfaeher Zugang zu l-Aryl-5-(2-dialkylaniino-vinyl)-lHtetrazolen 4 gefunden, die als Enamine von (1-Aryl-1H-tetrazol-5-yl)-aeetaldehyden (vgl. [ 13) 1-Aryl-5-[2-(N-alkyl-anilino)-rinyl] -1H-tetrazole 8a-k (vgl.…”

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Tetrazolverbindungen. 3. Modifizierung von (1‐Aryl‐1H‐tetrazol‐5‐yl)‐acetaldehyd‐Enaminen durch säurekatalysierte Umaminierung

Fischer

1988

J. Prakt. Chem.

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Tetrazole Compounds. 3. Modification of 1‐Aryl‐1H‐tetrazole‐5‐acetaldehyde Enamines by Acid‐Catalyzed Transamination The acid‐catalyzed transamination of tetrazole‐5‐acetaldehyde enamines proves to be a useful synthetic method for preparing specially N‐substituted enamines of this series not accessible directly from 3‐chloro‐propeniminium salts 3 and sodium azide. Thus, starting from (E)‐1‐aryl‐5‐(2‐dimethylamino‐vinyl)‐1H‐tetrazoles 5 transamination with dialkylamines yields tertiary enamines of types 6 and 7. Analogously, acid‐catalyzed reaction of 5 with N‐alkylanilines leads to 1‐aryl‐5‐[2‐(N‐alkylanilino)‐vinyl]‐1H‐tetrazoles 8. Bifunctinal secondary amines such as N,N′‐dimethylethylenediamine result in systems of type 9 with two linked tertiary tetrazolyvinylamino groups. All the transaminations with secondary amines proceed with retention of configuration. According to the same reaction scheme transamination of 5 (Ar = Ph) with primary alkyl‐, aralkyl‐, and arylamines affords secondary tetrazolylvinylamines 10; however, here the formation of Z‐configurated products dominates. Bifunctional primary amines like ethylenediamine and 1,2‐phenylenediamine react with 5 to give the N,N′‐linked systems 11 and 12 possessing two secondary tetrazolylvinylamino groups. – Characteristic i.r., u.v., and 1H‐n.m.r. spectroscopic data of the novel tetrazole‐5‐acetaldehyde enamines are reported.

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Tetrazolverbindungen. 3. Modifizierung von (1‐Aryl‐1H‐tetrazol‐5‐yl)‐acetaldehyd‐Enaminen durch säurekatalysierte Umaminierung

Fischer

1988

J. Prakt. Chem.

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ChemInform Abstract: Tetrazole Compounds. Part 1. 1‐Aryl‐5‐(2‐dialkylamino‐vinyl)‐1H‐tetrazoles from 3‐Chloropropeniminium Salts.

Fischer¹,

Herrmann²

1989

ChemInform

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Tetrazole compounds. 8. Synthesis of tetrazolylpyrimidines from tetrazolyl‐substituted enamino ketones

Fischer¹

1993

Journal of Heterocyclic Chem

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Tetrazolyl‐substituted enamino ketones 1 react with various amidines 2 to give 5‐(1‐phenyl‐1H‐tetrazol‐5‐yl)pyrimidines 3. In the case of the chloroacetyl enamine 4 4‐(N,N‐dimethylaminomethyl)‐substituted tetra‐zolylpyrimidines 5 were obtained. Subsequent hydrolysis of the 4‐trifluoromethyl derivatives 3b, 3d and 3g afforded the corresponding 5‐(1‐phenyl‐1H‐tetrazol‐5‐yl)pyrimidine‐4‐carboxylic acids 6.

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Tetrazolverbindungen. 1. 1‐Aryl‐5‐(2‐dialkylamino‐vinyl)‐1H‐tetrazole aus 3‐Chlor‐propen‐iminiumsalzen

Cited by 14 publications

References 15 publications

Tetrazolverbindungen. 3. Modifizierung von (1‐Aryl‐1H‐tetrazol‐5‐yl)‐acetaldehyd‐Enaminen durch säurekatalysierte Umaminierung

Tetrazolverbindungen. 3. Modifizierung von (1‐Aryl‐1H‐tetrazol‐5‐yl)‐acetaldehyd‐Enaminen durch säurekatalysierte Umaminierung

ChemInform Abstract: Tetrazole Compounds. Part 1. 1‐Aryl‐5‐(2‐dialkylamino‐vinyl)‐1H‐tetrazoles from 3‐Chloropropeniminium Salts.

Tetrazole compounds. 8. Synthesis of tetrazolylpyrimidines from tetrazolyl‐substituted enamino ketones

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