One-Pot Synthesis of Unsymmetrical Bis-Heterocycles: Benzimidazole-, Benzoxazole-, and Benzothiazole-Linked Thiazolidines

Abstract

A one-pot, three-component synthesis of benzimidazole-linked thiazolidines from 2-cyanomethyl benzimidazole, iso-, isothio-, or isoselenocyanates and 1,2-dichloroethane is reported. Isolation of the key intermediate formed during the course of the reaction validates its mechanistic pathway. Under the same reaction conditions, benzimidazole-linked/fused thiazinanes were obtained when 1,3-dichloropropane or diiodomethane was used.

Palladium-Catalyzed Synthesis of Linked Bis-Heterocycles─Synthesis and Investigation of Photophysical Properties

“…Heterocycles are privileged structural motifs in organic chemistry. − Their prominence in the fields of pharmaceutical, agrochemical, and materials research has led to countless methods designed for the facile construction of heterocyclic scaffolds from easily accessible building blocks . Linking two heterocycles to form a bis-heterocycle is of interest to access more complex molecular architectures with extended π-systems that lead to desirable optical properties . The synthesis of many bis-heterocyclic motifs are quite challenging, and thus, new methods to link two heterocycles has remained a topic of interest for over two decades. − Within this domain, bis-heterocycles with 2,2′- and 2,3′- linkages have shown enhanced potency as anticancer therapeutics and utility as fluorescent markers and provide access to a vast array of carbazole motifs for use in semiconductors and organic light-emitting diodes (OLEDs) (Scheme A).…”

“…1−3 Their prominence in the fields of pharmaceutical, agrochemical, and materials research has led to countless methods designed for the facile construction of heterocyclic scaffolds from easily accessible building blocks. 4 Linking two heterocycles to form a bis-heterocycle is of interest to access more complex molecular architectures 5 with extended πsystems that lead to desirable optical properties. 6 The synthesis of many bis-heterocyclic motifs are quite challenging, and thus, new methods to link two heterocycles has remained a topic of interest for over two decades.…”

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“…Heterocyclic compounds occupy central position in organic chemistry, and considerable attention has been focused on their synthesis. In particular, the benzof used nitrogen containing heterocycles are a common heterocyclic scaffold in many biologically active and medicinally significant compounds 7 .…”

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

“…[21a] Further, this strategy provides access to an unexplored pool of chemical entities that may display exceptional biological properties due to synergistic effects. [23] Besides, the compounds containing BHCs found potential applications in various fields such as Agrochemicals, optical materials, electrical materials, metalorganic frameworks, and polymer sciences [24] (See Figure 1. for representative examples).…”