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Reaktion von 3-Dimethylamino-2,2-dimethyl-2H-azirin mit Barbitursäure

✍ Scribed by Helmut Link; Karl Bernauer; John J. Daly; Stanislav Chaloupka; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
785 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Reaction of 3‐Dimethylamino‐2,2‐dimethyl‐2__H__‐azirine with Barbituric Acid

The reaction of 3‐dimethylamino‐2,2‐dimethyl‐2__H__‐azirine (1) with barbituric acid (4) in dimethyl formamide at room temperature yields a mixture of several compounds. The two main products 5 and 6 have been isolated in 40 and 10% yield, respectively, and their structures established by X‐ray analysis. In Schemes 4–6 reaction mechanisms for the formation of 5 and 6 are postulated, the first step beeing either a C‐ or an N‐alkylation of barbituric acid.

Reduction of 5 and 6 with NaBH~4~ in ethanol at room temperature yields 6,6‐dimethyl‐1,5,6,7‐tetrahydro‐pyrrolo[2,3‐d]pyrimidin‐2,4(3__H__)‐dione (7) and 3,3‐dimethyl‐2,3‐dihydro‐imidazo[1,2‐c]pyrimidin‐5,7(1__H__, 6__H__)‐dione (8) in 38 and 48% yield, respectively. Treatment of 6 with 3N aqueous NaOH at room temperature gives 3,3‐dimethyl‐imidazo[1,2‐c]pyrimidin‐2,5,7 (1__H__, 3__H__, 6__H__)‐trione (9) in 51% yield (Scheme 3).

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**Reaction of 3‐Dimethylamino‐2,2‐dimethyl‐2__H__‐azirine with Phenyl Isothiocyanate** In contrast to the reactions of 3‐dimethylamino‐2,2‐dimethyl‐2__H__‐azirine (**1a**) with various isothiocyanates, leading to thiazoline derivatives, the reaction of **1a** with phenyl isothiocyanate at room temp

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**Reaction of 3‐Dimethylamino‐2,2‐dimethyl‐2__H__‐azirine with 6‐Methyluracil; Crystal Structure of the Products** The reaction of 3‐dimethylamino‐2,2‐dimethyl‐2__H__‐azirine (**1**) with 6‐methyl‐uracil (**4**) in 2‐propanol at 80° yields the 4__H__‐imidazoje derivative **5** as the main product.

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**Addition Reaction of 3‐Dimethylamino‐2,2‐dimethyl‐2__H__‐azirine with Phenylisocyanate and Diphenylketene** 3‐Dimethylamino‐2,2‐dimethyl‐2__H__‐azirine (**1a**) reacts with carbon disulfide and isothiocyanates with splitting of the azirine N(1), C(3)‐double bond to give dipolar, fivemembered hete

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## Abstract 2,2‐Dimethyl‐3‐dimethylamino‐2__H__‐azirine (**1**) reacts with the formyl‐cycloalkanones **4**–**8** in boiling benzene to give the 1:1 adducts **13**–**17** in 60–99% yield (Table). These adducts are N′‐[(2‐oxo‐cycloalkylidene)‐methyl] derivatives of 2‐amino‐N, N‐dimethylisobutyramide