Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

• Francesco Gambuti,
• Jacopo Pizzorno,
• Chiara Lambruschini,
• Renata Riva and
• Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

• Francesco Gambuti Jacopo Pizzorno Chiara Lambruschini Renata Riva Lisa Moni Department of Chemistry and Industrial Chemistry, University of Genoa, Via Dodecaneso 31, 1646 Genova, Italy 10.3762/bjoc.20.230 Abstract Spiro-heterocyclic indolenines are privileged scaffolds widely present in numerous

• -indolenines, specially the spiro-heterocyclic indolenines, can be considered as a privileged scaffold, present in several natural products with interesting biological activities, as depicted in Figure 1 [4][5][6][7]. Among the known methods of synthesizing spiro-heterocyclic indolenines, the dearomative

• spiro-heterocyclic indolenines from readily available starting materials under mild conditions and in a diversity-oriented fashion remains desirable. In this contest, oxidative isocyanide-based multicomponent reactions (oxidative IMCRs) can be considered as a convenient tool [15]. Actually, the use of

Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

• Anup Biswas

Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72

• enantioselective aza-Friedel–Crafts addition. In the first step, the DDQ-promoted oxidation of 3-indolinonecarboxylate 22 generated indolenines that performed as the potential electrophiles towards indoles 4. The chiral catalyst effectively assembled the reacting partners in a chiral transition state through H

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

• Aleksandar Pashev,
• Nikola Burdzhiev and
• Elena Stanoeva

Beilstein J. Org. Chem. 2020, 16, 1456–1464, doi:10.3762/bjoc.16.121

• aromatic heterocycles have a low tendency to undergo reactions with cyclic anhydrides, resulting in low to moderate overall yields of the target products [12][27]. Further research by Krasavin et al. on the reactivity of sterically hindered indolenines in reactions with anhydrides 6–9, did not give the

A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline

• Olga Bakulina,
• Alexander Ivanov,
• Vitalii Suslonov,
• Dmitry Dar’in and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138

• substantial degree of steric encumbrance has been prepared via a novel variant of the Castagnoli–Cushman reaction of homophthalic anhydride (HPA) and various indolenines. The employment of a special kind of a cyclic imine component reaction allowed, for the first time, isolating a Mannich-type adduct between

• HPA and an imine component which has been postulated but never obtained in similar reactions. Keywords: Castagnoli–Cushman reaction; diastereoselectivity; homophthalic anhydride; indolenines; lactam synthesis; multicomponent reactions; Introduction The reaction of imines (prepared in a separate step

• plethora of biological activities displayed by the lycorine and tylophorine alkaloids (such as pro-apoptotic [22], antiviral [23], hypoxia-inducible factor-1 inhibitory [24]), the scaffold can be confidently regarded as privileged [25]. Recently, we [26] and others [27] reported the use of indolenines as