蟺-Aromatic and Sulfur Nucleophilic Partners in Cationic 蟺-Cyclizations: Intramolecular Amidoalkylation and Thioamidoalkylation Cyclization via 蠅-Carbinol Lactams was written by Hucher, Nicolas;Decroix, Bernard;Daiech, Adam. And the article was included in Journal of Organic Chemistry in 2001.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:
NaBH4 reduction of imides followed by a 蟺-cyclization of the resultant N-acyliminium ions, generated in trifluoroacetic acid conditions, afforded two positional isomers, isoindolobenzothiazolinones. These ring closures proceeded via an intramol. 伪-amidoalkylation with the classical 蟺-aromatic or the atypical sulfur atom as an internal nucleophile. A ready access to the related six-membered N,S-heterocyclic compounds such as isoindolobenzothiazinones is also described. During this reaction, we have shown that a 蠅-carbinol lactam precursor led to endocyclic and exocyclic N-acyliminium ions in equilibrium via the a cyclic aza-sulfonium ion. The latter furnished the expected products in good yields. Similarly, different 蠅-carbinol lactams substituted at C-angular position afforded the corresponding isoindolobenzothiazinones bearing an angular alkyl, aralkyl, or aryl group. In the case of Me and benzyl groups, an addnl. amount of the dehydration products was isolated. These results indicate that the isomerization-蟺-cyclization takes place via the cleavage of the thioether linkage in acidic medium. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Quality Control of 2-(Phenylthio)isoindoline-1,3-dione).
2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles