Biologically Active Compounds. III. The Synthesis of α-Alkylamino-α-arylacetamides

A series of α-monoalkylamino-α-arylacetamides and α-dialkylamino-α-arylacetamides have teen synthesized via the corresponding nitriles. Some of these compounds have been found to exhibit moderate activity as herbicides

Lactone Carboxylic Acids. IV. Reaction of Ethyl Chloroarylpyruvate with Ethyl Malonate

The condensation of ethyl chloroarylpyruvate (Ⅰ) with ethyl malonate in the presence of sodium ethoxide afforded γ-aryl-α,β-dicarbethoxy-⊿(β),γ-butenolide. On the basis of the chemical and spectral evidences, the structure of the product (II) has been elucidated. This reaction provides new routes to α,β-dicarboalkoxy-γ-butyrolactones and/or to γ-ketocarboxylic acids

New Stable Sulfonium Ylides. 1-Dimethylsulfuranylidene-l-phenylsulfonyl-2-propanone and Related Compounds

The preparation of the title compounds as a new type of stable S-ylides has been described. The reaction of 1-dimethylsulfuranylidene-1-phenylsulfonyl-2-propanone (IIb) with lithium aluminium hydride was found to result in the formation of trans-phenylpropenylsulfone (IV), phenylsulfonyl-2-propanone (Ib), and an unidentified paraffin as major products

Reaction of α-Chloro-N-arylisobutyrimidyl Chloride with Ethyl Malonate(1)

a-Chloro-N-arylisobutyrimidyl chloride (I) reacted with ethyl sodiomalonate to afford N-aryl-2,2-dimethyl-3 carbethoxysuccinimide. This reaction seems to proceed in a different mechanism from that of the synthesis of tetronic acids(2) and is supposed to involve a primary attack of the carbanion at the a-carbon atom of the chloride followed by the cyclization

Biologically Active Compounds. IV. The Synthesis of α-Arylamino-γ-aryl-⊿(α,β)- and α-Arylidene-γ-aryl-⊿(β,γ)-butenolides.

The importance of the presence of butenolide groupings in biologically active substances has been recognized increasingly. (1) In our search for new pesticides we have prepared 26 α-arylamino-γ-aryl-⊿(α,β)-butenolides (1-26) and 9 α-arylidene-γ-aryl-⊿(α,β)-butenolides (27-35) which seemed to us of interest as test materials for the screening. α-Arylamino-γ-aryl-⊿(α,β)-butenolides were prepared by the reaction of sodium or potassium arylidenepyruvate with arylamines in the medium of glacial acetic acid as is reported by Meyer and Vaughan(2) (Scheme I, see also Experimental Section). α-Arylidene-γ-aryl-⊿(β,γ)-butenolides were prepared by the condensation of aromatic aldehydes with β-aroylpropionic acids in the presence of anhydrous sodium acetate. The analogous procedure for this purpose has been reported by several authors(3) (Scheme II). The physical properties, yields, and analytical data of these compounds have been summarized in Table I (1-26) and Table II (27-35)