Synthesis of amino‐5‐arylsulfonylpyrimidines

Abstract

Several new 4‐amino‐5‐arylsulfonylpyrimidines were prepared via the reaction of various α‐(ethoxymethylene)arylsulfonylacetonitriles with guanidine or variously substituted amidines (Table II). 2,4‐Diamino‐5‐(p‐chlorophenylsulfonyl)pyrimidine (IIIg), a typical example, was prepared from the reaction of 2‐(p‐chlorophenylsulfonyl)‐3‐ethoxyacrylonitrile (IId) with guanidine in refluxing ethanol containing sodium ethoxide. With proper substitution of the ethoxymethylene intermediate, the method was found suitable for the preparation of other compounds having either a hydroxy or methyl group at the 4‐position of the 5‐arylsulfonylpyrimidine. The fluoro group in 2,4‐diamino‐5‐(p‐fluorophenylsulfonyl)pyrimidine (IIIx) was successfully replaced by nucleophilic reagents such as sodium ethoxide, N‐methylpiperazine and N,N‐diethylethylene‐diamine. Attempts at direct displacement of fluorine by ammonia at 190° were unsuccessful.

Some New Routes for the Preparation of 3-Amino-2-phenyl-4(1H)-quinolinones from Anthranilamides

“…The key intermediate 2a (and analogues) has been proposed several times in the literature , but has not been previously isolated. These compounds were prepared by reaction of the commercially available 2-aminoacetophenones 1a − k with isatoic anhydride, following a method similar to that employed for the synthesis of a chloro analogue . Diazepinone 4a has been prepared, and its melting point is reported in the literature, but we have found that, in contrast to the previous report, use of piperidine as a catalyst led to a less clean reaction.…”

Development of the Applications of Palladium on Charcoal in Organic Synthesis

“…In the past, 1,4‐benzodiazepines were primarily used in central nervous system therapies. They have now been extended to antibiotic, antimalarial, anti‐HIV, anticancer, antidepressant, antitumour, anti‐insectant, analgesic, and fibrinogenic receptor antagonist drugs . Therefore developing efficient methodologies for the synthesis of these diverse scaffolds has attracted much attention.…”

α(β)-Sulfonyl(phosphoryl)acrylonitriles and enamines in the synthesis of biologically active heterocycles

“…За цією ж схемою на основі вихідних сполук 59 (ще один різновид етоксіакрилонітрилів на зразок сполук 1) та амідинів 60 було одержано похідні 4-аміно-5-арилсульфонілпіримідинів 61 [26] (схема 21). Як структурні ізомери відомих на той час сульфаніламідів (наприклад, сульфадимідину) отримані в цій роботі піримідини були перевірені на антибактеріальну дію, але очікуваного рівня активності ці сполуки не мали; натомість во-ни виявили гіпотензивні та знеболювальні властивості.…”