A novel and efficient method for the synthesis of heteroannulated [1,4]benzodiazepines via an isocyanide-based multicomponent reaction is reported. The tetrazolo[1,5-a][1,4]benzodiazepines were obtained by a facile azide Ugi five-center four-component (U-5C-4CR) using ketones, sodium azide, ammonium chloride, corresponding isocyanide. aforementioned tetrazolodiazepines represent notable class compounds with proven platelet aggregation inhibitory cholecystokinin agonist activities.

Rh(II)-catalyzed decomposition of α-diazo homophthalimides in the presence cyclic ethers gave spirocyclic products Stevens-type [1,2]-alkyl shift within postulated oxonium ylide intermediate. Such a reaction pathway is line with thermodynamic predictions obtained from quantum chemical calculations performed at B3LYP/6-31G* and B3LYP/6-311++G** levels theory. These findings represent first systematically investigated case spirocyclization α-diazocarbonyl compounds ethers.

Hitherto undescribed 3-unsubstituted tetrahydroisoquinolonic acids (isolated as their respective methyl esters) were accessed for the first time by uncatalyzed, thermally promoted Castagnoli–Cushman reaction (CCR) of homophthalic anhydride (HPA) and a series 1,3,5-triazinanes. The moderate yields observed in some cases are most likely associated with persistent impurity also formed these reactions. new scaffold is expected to find novel medicinal utility (compared traditional CCR adducts)...

A novel effective protocol towards indolo[2,1-<italic>a</italic>]isoquinolinones <italic>via</italic> aryne-induced migration of aryl-anion in aryloxy substituted 3,4-dihydroisoquinolines is reported.

Protonation of 4-diazoisoquinoline-1,3(2H,4H)-diones in Brønsted acids gives rise to diazonium cations that can be trapped with arenes give 4-arylisoquinoline-1,3(2H,4H)-diones (homophthalimides). This provides a new, metal-free approach 4-aryltetrahydroisoquinolines (obtainable from respective homophthalimides by reduction). Similarly, fluorine atom introduced trapping the cation HF. led preparation first examples 4-monofluoro-substituted isoquinoline-1,3-diones (as well as their...

The earlier reported three-component Castagnoli-Cushman-type synthesis of 1,4,6-trisubstituted 1,6-dihydropyridin-2-(3H)-ones from 3-arylglutaconic acids, primary amines, and aromatic aldehydes has been further investigated. It was shown to proceed via anhydrides, which, in turn, were found give superior results the two-component reactions with imines. initial formation Castagnoli-Cushman carboxylic acids be case, their decarboxylation follow a complex, "forked" pathway, which confirmed by...

Abstract The reactivity pattern of the Castagnoli‐Cushman reaction between homophthalic anhydride and imines was completely reproduced by replacing with o ‐(alkoxycarbonyl)methyl benzoic acids activated CDI (1,1′‐carbonyldiimidazole). This allows obtaining tetrahydroisoquinolonic esters directly plants chemistry onto a fundamentally new reagent space not requiring use cyclic anhydrides.

Abstract Tetramic acids exhibit intriguing biological activity and are particularly attractive scaffolds for drug design. In this paper, we present a convenient approach based on the Dieckmann cyclization of Ugi adducts malonic monoesters to afford series medically important polysubstituted tetramic acid derivatives. This simple versatile method tolerates various substituents in both amine, aldehyde isocyanide moieties allowing use α‐substituted monoesters. Examples further functionalization...

a-Diazo carbonyl compounds are widely used as reagents of vast synthetic potential, capable delivering biologically relevant and diverse molecular scaffolds. Herein we present methods for selective N -alkylation various diazo NH-heterocycles while maintaining the function further modifications. homophthalimide, arylidene succinimides, barbituric thiobarbituric acids, a-diazo pyrazolones were readily alkylated with alkyl halides or alcohols under Mitsunobu reaction conditions. This is first...

Chalcone imines were reacted with homophthalic anhydrides to serve as a four-atom building block in [4+2]-formal cycloaddition reaction unexpected chemoselectivity (Castagnoli–Cushman-type reaction), providing dihydropyridin-2(1<italic>H</italic>)-ones.

In the present study, a new synthetic strategy towards N ‐acylated glycinamides was developed by use of 1,3,5‐triazinanes as formaldimine surrogates in Ugi reaction. The targeted products were obtained combinatorial, diversity‐oriented fashion good yields. Further modifications allowed us to adapt this procedure for one‐pot two‐step syntheses local anesthetic druglidocaine and several unsymmetrically substituted diketopiperazines.

Abstract An underexplored type of heterocyclic α‐diazocarbonyl compounds, α‐diazo glutaconimides was involved in the generation oxonium ylide species by Rh(II) catalysis presence tetrahydrofuran and 1,4‐dioxane. The formation a spirocycle through formal Stevens‐type O → C [1,2]‐shift within case THF low‐yielding accompanied known [1,4]‐shift to give fused bicyclic products. Reactions with 1,4‐dioxane proved noticeably higher‐yielding respect target spirocycle. In this case, however, observed...

Based on the previously reported involvement of homophthalic acid monoesters in Castagnoli-Cushman reaction-type cyclocondensation with imines, we tested a number other o-methyl benzoic acids bearing various electron-withdrawing groups α-position. The majority these substrates delivered expected tetrahydroisoquinolone adducts activation CDI or acetic anhydride. Homophthalic mononitriles displayed highest promise as for new reaction, both terms scope and product yields. monoamides either gave...