A Lewis Acid-Catalyzed Cascade Synthesis of Fused -Heterocycles from 2-Alkynylanilines and 2-Formylbenzonitriles: Unveiling Iminoisoindoloindolone and Its Derivatives.

We herein reveal a streamlined synthesis of structurally fused 6-iminoisoindoloindolones via a meticulously orchestrated cascade reaction. This process seamlessly intertwines 2-alkynylaniline and 2-formylbenzonitrile under the catalytic influence of TMSOTf, giving rise to these compounds in remarkable yields that stand as a testament to the efficiency of our approach. Moreover, the versatility of this synthetic strategy extends far beyond mere synthesis, offering a gateway to the creation of both isoindoloindolone and unprecedented diphenylbenzopyrrolizinoisoquinolinone derivatives, thereby opening new horizons in the realm of chemical innovation.

Synthesis of Highly π-Extended Dihydrobenzo[]indenocarbazole Scaffolds via Tandem Benzannulation and Friedel-Crafts Reaction of 2-Alkynylanilines and 2-Alkynylbenzaldehydes Promoted by Lewis Acid.

A novel and efficient tandem protocol for the swift synthesis of dihydrobenzo[]indenocarbazole frameworks from 2-alkynylanilines and 2-alkynylbenzaldehydes via BF·OEt-facilitated benzannulation and Friedel-Crafts reaction has been described. This innovative approach accommodates a wide array of functional groups, offering a myriad of diversified carbazole products. Later, postsynthetic modification leads to its C(sp)-H hydroxylation.

Synthesis of Benzodioxepinones and Benzoxazepinones via Tandem Oxidation and Iodolactonization of 2-/-tethered Alkenyl Benzaldehyde Mediated by CuI/TBHP.

An efficient methodology for the synthesis of halogenated benzodioxepinones and benzoxazecinones has been developed via tandem oxidation and iodolactonization reaction of 2-/-tethered alkenyl benzaldehydes mediated by CuI and tertiarybutylhydro-peroxide in acetonitrile at 70 °C in moderate to good yields. The reaction involves initial oxidation of aldehyde to acid followed by iodolactonization. Terminal propargyl ether resulted in a mixture of mono- and diiodido-3-methylene-1,4-dioxepin-5-ones.

Temperature Tunable Synthesis of Tetrahydro-4-pyrrolo[3,2-]quinolin-4-ones and Dihydro-1-benzo[]azepines from 2-Aminobenzonitriles and Donor-Acceptor Cyclopropanes.

Tetrahydro-4-pyrrolo[3,2-]quinolin-4-ones and dihydro-1-benzo[]azepines are efficiently synthesized from 2-aminobenzonitriles and donor-acceptor cyclopropanes mediated by SnCl in moderate to good yields. The reaction involves the initial ring opening of a cyclopropane ring due to activation by SnCl followed by nucleophilic attack by amine to give an adduct, which after unprecedented rearrangement at two different reaction temperatures provides two nitrogen heterocyclic compounds. This methodology can be used for the synthesis of hexahydropyrrolo[3,2-]quinolinone derivatives, the structure of which is found in biologically active molecules.