133523-76-9

Upstream product

• 34021-60-8 N-(3-hydroxy-3-methylbutyl)benzamide 
• 13156-33-7 N-(3-methylbut-2-en-1-yl)benzamide 

Downstream Products

• 133523-67-8 5-(1-Bromo-1-methyl-ethyl)-2-phenyl-4,5-dihydro-thiazole 
• 133523-86-1 5-(1-Methyl-1-phenylselanyl-ethyl)-2-phenyl-4,5-dihydro-thiazole 
• 133523-90-7 5,6-Dihydro-6,6-dimethyl-2-phenyl-4H-1,3-thiazine 
• 133523-91-8 5-Isopropyl-2-phenyl-2-thiazoline 
• 133523-68-9 5-Isopropenyl-2-phenyl-4,5-dihydro-thiazole 

Relevant academic research and scientific papers

Reaction of (1,ω)-N-Acylamino Alcohols with Lawesson's Reagent: Synthesis of Sulfur-Containing Heterocycles

Lawesson's reagent [LR: 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiaphosphetane 2,4-disulfide] is shown to be a valuable reagent for the ready access of sulfur-containing heterocycles: thiazolines 2 starting from the (1,2)-N-acylamino alcohols 1 and benzothiazines 14 from [2-(N-acylamino)phenyl]alkanols 12. Treatment of (1,2)-N-acylamino secondary alcohols 1a-p with LR gave the thiazolines 2a-p via direct conversion of the alcohols to the respective thiols, and the subsequent thionation of the amide carbonyl, followed by cyclization with the elimination of hydrogen sulfide. However, reaction of (1,2)-N-acylamino tertiary alcohols 1q-u with LR yielded the dehydration products 5-7 and 9. Treatment of [2-(N-acylamino)phenyl]alkanols 12a-f with a molar equivalent of LR yielded the 3,1-benzothiazines 14a-f. In this reaction, the [2-(N-acylamino)phenyl]alkanethiols 13a-e were isolated when the corresponding alcohols 12a-e were treated with 0.5 equiv of LR. Further thionation of 13c with LR also gave 3,1-benzothiazine 14c.

Organoselenium- and Proton-Mediated Cyclization Reactions of Allylic Amides and Thioamides. Syntheses of 2-Oxazolines and 2-Thiazolines

A variety of allylic amides and thioamides were treated with phenylselenenyl bromide in chloroform to give, via 5-exo cyclization, 2-oxazolines and 2-thiazolines, respectively, carrying a (phenylselenenyl)methyl substituent in the 5-position.In some cases (N-crotyl- and N-cinnamylamides/thioamides), dihydro-1,3-oxazines/-thiazines were formed via 6-endo cyclization.The phenylselenenyl group of the cyclofunctionalization products was slowly eliminated by treatment with m-chloroperbenzoic acid to introduce unsaturation in the resulting oxazoline/thiazoline.Reductive removal of the phenylselenenyl group was effected by treatment with triphenyltin hydride.This reaction was sometimes accompanied by a rearrangement of the heterocyclic ring.Proton-induced cyclizations of allylic thioamides to give 2-thiazolines was slowly but efficiently effected in boiling toluene containing a catalytic amount of p-toluenesulfonic acid.