Direct synthesis of 1-naphthylamines enabled by 6-endo-dig cyclization strategy using copper catalysis was written by Ma, Peng;Wang, Jianhui;Liu, Guiyan. And the article was included in Applied Organometallic Chemistry in 2022.Category: benzothiophene This article mentions the following:
A facile approach for the synthesis of substituted 1-naphthylamines I [R1 = Ph, 2-FC6H4, 3-ClC6H4, etc.; R2 = H, 7-F, 6-Cl, etc.; R3 = H, CH2CH=CH2; R4 = Ph, Bn, Cy, etc.; R3 = R4 = Me; R3R4 = CH2CH2OCH2CH2] via three-component 6-endo-dig cyclization of terminal alkynes with 2-bromoaryl ketones, primary or secondary amines in water under Pd-free conditions was described. The Cu(I) catalytic system avoided a fundamental problem related to these substrates, which competitively evolve through 5-endo-dig cyclization pathways under metal catalysis. This unique performance unlocked a rapid access to a diverse 1-naphthylamines library that previously required longer synthetic routes. The synthetic potential of this method was further demonstrated by the gram-scale synthesis, and the mechanism study showed that the reaction experienced sequential halide exchange, imine-enamine tautomerization and 6-endo-dig cyclization. In the experiment, the researchers used many compounds, for example, 3-Ethynylthiophene (cas: 67237-53-0Category: benzothiophene).
3-Ethynylthiophene (cas: 67237-53-0) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Category: benzothiophene
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem