Naphtholactam Explained

Naphtholactam is an organic compound derived from naphthalene. It is a tricyclic species consisting of a naphthalene core fused with a lactam (NH-CO-) at the 1,8-positions. The N-alkyl derivatives are commercially important.

Dye precursor

It is a precursor to the dye anthanthrone via ring-opening to the amino carboxylic acid, which can be converted to the diazonium salt. Naphthostyril derivatives are also of interest in medicinal chemistry.^[1] Naphthostyrils can be produced by metal-catalyzed cyclization of 1-naphthylamides.^[2] N-Ethylnaphtholactam and related derivatives are precursors to many dyes. The lactam condenses with anilines in the presence of phosphorus oxychloride.

References

1. 10.1021/jm030841r. Optimization of the Pharmacophore Model for 5-HT7R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives. 2003. López-Rodríguez. María L.. Porras. Esther. Morcillo. M. José. Benhamú. Bellinda. Soto. Luis J.. Lavandera. José L.. Ramos. José A.. Olivella. Mireia. Campillo. Mercedes. Pardo. Leonardo. Journal of Medicinal Chemistry. 46. 26. 5638–5650. 14667218. 10637/5547. free.
2. 10.1021/acs.orglett.9b02037. Cobalt-Catalyzed Direct Carbonylative Synthesis of Free (NH)-Benzo[cd]indol-2(1H)-ones from Naphthylamides. 2019. Ying. Jun. Fu. Lu-Yang. Zhong. Guoqiang. Wu. Xiao-Feng. Organic Letters. 21. 14. 5694–5698. 31246481.