Mechanistic study on rearrangement cascades starting from annulated 2-aza-hepta-2,4-dienyl-6-ynyl anions: formation of aniline and azepine derivatives was written by Lyaskovskyy, Volodymyr;Froehlich, Roland;Wuerthwein, Ernst-Ulrich. And the article was included in Chemistry – A European Journal in 2007.Related Products of 6287-82-7 This article mentions the following:
Deprotonation of benzothiophene-derived alkynyl imine 11 with lithium diisopropylamide (LDA) and subsequent transmetalation with ZnCl2 etherate furnished azepine 12 upon aqueous workup. Similarly, alkynyl benzaldimine 1a gave a mixture of benzazepine 13 and naphthylamine 14. Allylic benzonitriles 15a,b reacted to produce naphthylamine 16 upon deprotonation with LDA at room temperature In an analogous manner, imino benzonitrile 17 may be converted into 4-amino isoquinoline 18 by means of an intramol. nucleophilic attack on the nitrile function upon treatment with LDA. The allylic benzonitriles 19a,b were prepared by LDA treatment of alkynyl imine 11. They were further converted to amino dibenzothiophene 20 by LDA deprotonation and aqueous workup. These various transformations represent tile key steps of a multistep reaction cascade, which was previously postulated on the basis of quantum chem. calculations Thus, all features of this complex rearrangement mechanism could now be confirmed exptl. DFT calculations support the lower reactivity of zinc species in the ring-opening step compared to the lithium intermediates. All new compounds were completely characterized by spectroscopic data, including X-ray diffraction studies for the key compounds 12, 19a, and 20. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Related Products of 6287-82-7).
2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It is also used in the manufacturing of dyes such as thioindigo.Related Products of 6287-82-7
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem