scholarly journals Studies on Isothiazoles. III. A Novel Ring Closure to Isothiazoles by the Reaction of α-Amino Ketones with Thionyl Chloride or Sulfur Monochloride

1968 ◽  
Vol 41 (4) ◽  
pp. 959-964 ◽  
Author(s):  
Takayuki Naito ◽  
Susumu Nakagawa ◽  
Jun Okumura ◽  
Kiyoshi Takahashi ◽  
Ken-ichi Kasai
Keyword(s):  
Thionyl Chloride ◽  
Ring Closure ◽  
Sulfur Monochloride

Acetylenic acids. II. The reaction of sulfur chlorides with phenylpropiolic acid and its methyl ester

1978 ◽  
Vol 31 (3) ◽  
pp. 605 ◽  
Author(s):  
WN Lok ◽  
AD Ward
Keyword(s):  
Methyl Ester ◽  
Acid Chloride ◽  
Thionyl Chloride ◽  
Sulfuryl Chloride ◽  
Acid Form ◽  
Sulfur Monochloride ◽  
Sulfur Dichloride ◽  
Acetylenic Acids

The reactions of phenylpropiolic acid and methyl phenylpropiolate with thionyl chloride, sulfur monochloride, sulfur dichloride and sulfuryl chloride have been investigated. With thionyl chloride the presence of pyridine is necessary for a reaction to occur with the ester or for the reaction to proceed beyond the acid chloride stage in the case of the acid. In all cases the Z and E isomers of 2,3-dichlorocinnamic acid or its methyl ester are among the main products that have been identified. With all but sulfuryl chloride a 3-chloro-1-benzothiophen system is also formed. Sulfuryl chloride and phenylpropiolic acid form 4-chloro-1-phenylnaphthalene-2,3-dicarboxylic anhydride in low yield. The structures of other minor products and the pathways leading to all these products are discussed.

Acetylenic Acids. IV. The Reactions of Alkoxy-Substituted Phenylpropiolic Acids and Esters with Sulfur Halides, Particularly Thionyl Chloride

1979 ◽  
Vol 32 (4) ◽  
pp. 833 ◽  
Author(s):  
CM Bonnin ◽  
PA Cadby ◽  
CG Freeman ◽  
AD Ward
Keyword(s):  
Thionyl Chloride ◽  
Major Product ◽  
Sulfur Monochloride ◽  
Sulfur Dichloride ◽  
Substituted 1 ◽  
Acetylenic Acids

3,4-Dialkoxy-substituted phenylpropiolic acids and esters react with thionyl chloride to give good yields of substituted 1-benzothiophen systems. Similar reactions of m-and p-methoxyphenylpropiolic acids and 3,4,5-trimethoxyphenylpropiolic acid, which yield mixtures of products, are reported. In contrast, 2,5- and 2,3-dimethoxyphenylpropiolic acids gave mixtures in which a coumarin is the major product. The effect of adding pyridine to the reaction mixture is outlined. Reactions involving sulfur monochloride and sulfur dichloride generally gave much lower yields of these products. Attempts to form organometallic intermediates from the 3-chloro-1-benzothiophen products were unsuccessful.

Ring Closure Matrix

2015 ◽  
Vol 19 (3) ◽  
pp. 274-281
Author(s):  
Milan Randic ◽  
Marjana Novic ◽  
Dejan Plavsic
Keyword(s):  
Ring Closure

Some 1-substitution derivatives of 4-aryl-2,3-dihalogeno-1-naphthols

1984 ◽  
Vol 49 (1) ◽  
pp. 110-121 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Milan Mělka
Keyword(s):  
Thionyl Chloride ◽  
Oxirane Ring ◽  
Secondary Amines ◽  
Two Phase ◽  
Lytic Effect ◽  
Primary And Secondary Amines ◽  
Phase Medium ◽  
Chloro Derivatives ◽  
Derivatives Of

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.

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