Three‐Component Coupling Reactions of Maleimides, Thiols, and Amines: One‐Step Construction of 3,4‐Heteroatom‐functionalized Maleimides by Copper‐Catalyzed C(sp²)−H Thioamination

Abstract

A copper-catalyzed intermolecular thioamination of maleimides with thiols and amines has been developed. A diverse range of 3-amino-4-thiomaleimides and 3,4-dihydropyrrolo [3,4-b][1,4] thiazine-5,7(2H,6H)-diones were obtained with good yields, involving CÀN and CÀS bond formations. This methodology is very practical and features high atom economy, excellent functional group tolerance.

Metal‐Free, PhI(OAc)2‐Promoted Oxidative C(sp2)−H Difunctionalization: Synthesis of Thioaminated Naphthoquinones

“…[53,54] In recent times, the intermolecular thioamination of maleimides has been reported with copper catalyst; otherwise, this type of direct coupling of maleimides with amines and thiols are very rare in literature. [55,56] In this work, we have observed that the thioamination of maleimide derivatives occurred with ease under the same standard conditions and notably, acetonitrile was found suitable as a solvent for this transformation (Table 3). At the starting step, N-phenyl substituted maleimide, 1 b successfully underwent this oxidative coupling reaction with substituted benzenethiol (p-CH 3 , p-Cl) and cyclic secondary amines like pyrrolidine, piperidine to afford the final thioaminated products 5 a, 5 b and 5 c respectively with moderate to good yields.…”

The Solid-State Structures of Cyclic NH Carboximides

“…Crystals 2020, 10, x FOR PEER REVIEW 6 of 50 Compound 30 forms C(8) chains by interaction of the imide NH with the remote ester carbonyl oxygen and these are cross-linked by the ring NH to nitro group C (10) interaction resulting in a two-dimensional network containing R 4 4 (31) units (Figure 11) [35]. Compound 31 forms dimers of pattern A by imide NH to CO interaction and these are then further linked in a zig-zag arrangement by dimer formation between the other imide CO and the six-membered ring NH (Figure 12) [36]. This gives an overall designation of C (10) Compound 31 forms dimers of pattern A by imide NH to CO interaction and these are then further linked in a zig-zag arrangement by dimer formation between the other imide CO and the six-membered ring NH (Figure 12) [36].…”

“…Compound 31 forms dimers of pattern A by imide NH to CO interaction and these are then further linked in a zig-zag arrangement by dimer formation between the other imide CO and the six-membered ring NH (Figure 12) [36]. This gives an overall designation of C (10) Compound 31 forms dimers of pattern A by imide NH to CO interaction and these are then further linked in a zig-zag arrangement by dimer formation between the other imide CO and the six-membered ring NH (Figure 12) [36]. This gives an overall designation of C(10)[ R 2 2 (8), R 2 2 (10)].…”

“…This gives an overall designation of C(10)[ R 2 2 (8), R 2 2 (10)]. Compound 31 forms dimers of pattern A by imide NH to CO interaction and these are then further linked in a zig-zag arrangement by dimer formation between the other imide CO and the six-membered ring NH (Figure 12) [36]. This gives an overall designation of C (10)…”

Diverse 3-Methylthio-4-Substituted Maleimides through a Novel Rearrangement Reaction: Synthesis and Selective Cell Imaging

“…Sulfur-containing disubstituted maleimides are traditionally accessed by several reaction steps, such as the reaction of nitroketene dithioacetal and phenylacetonitriles, , and hence, much effort has been devoted to the development of simpler and accessible methodologies for the preparation of these heterocycles. In this context, Zhao and co-workers, employing the nonsubstituted maleimide as a substrate, synthesized a 3-indolyl-4-thioarylmaleimide in three steps, including a copper iodide-catalyzed thiolation reaction (Scheme A) . Recently, Wu and co-workers were able to achieve 3-methylthio-4-arylmaleimides using simple reactants through a thiol-free annulation strategy promoted by iodide (Scheme B). , The main disadvantage of this protocol is the generation of iodomethane as a hazardous byproduct.…”