Indium-catalyzed annulation of o-acylanilines with alkoxyheteroarenes: synthesis of heteroaryl[b]quinolines and subsequent transformation to cryptolepine derivatives was written by Yonekura, Kyohei;Shinoda, Mika;Yonekura, Yuko;Tsuchimoto, Teruhisa. And the article was included in Molecules in 2018.Synthetic Route of C9H9NO3 This article mentions the following:
An efficient method for the synthesis of heteroaryl[b]quinolines such as I [R = H, 4-OH, 2,3-di-MeO, etc.; R1 = Me, i-Pr, Ph, etc.; X = N, S] was developed via annulation of o-acylanilines and MeO-heteroarenes using an indium Lewis acid as catalyst for tandem N-C and C-C bond formation. A series of indolo[3,2-b]quinolines was subsequently transformed to structurally unprecedented cryptolepine derivatives Mechanistic studies showed that the N-C bond formation was followed by the C-C bond formation. The indium-catalyzed annulation reaction thus started with the nucleophilic attack of the NH2 group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an SNAr fashion and thereby the N-C bond was formed. The resulting intermediate then cyclized and gave C-C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, provided the HA[b]Q after aromatizing dehydration. In the experiment, the researchers used many compounds, for example, 1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2Synthetic Route of C9H9NO3).
1-(6-Aminobenzo[d][1,3]dioxol-5-yl)ethanone (cas: 28657-75-2) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Synthetic Route of C9H9NO3
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem