1,4-Oxazepines and 1,4-Thiazepines

Dehaen, Wim; Ngo, Thien H.

doi:10.1016/b978-008044992-0.01209-8

Cited by 10 publications

(7 citation statements)

References 175 publications

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“…The N ‐containing [6,7] fused compounds are important heterocyclic scaffolds of immense biological and pharmacological significance [106–107] . These scaffolds are versatile building blocks for the creation of many biologically active natural products and drugs [108] . These structural motifs have also been widely explored for their medicinal and biological properties such as anticancer, antidepressant, antianxiety, anticonvulsant, antiarrhythmics, vasopressin antagonists etc [109–111] .…”

Section: Seven‐membered Heterocyclesmentioning

confidence: 99%

One‐Pot Multicomponent Reaction: A Highly Versatile Strategy for the Construction of Valuable Nitrogen‐Containing Heterocycles

et al. 2022

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A large portion of the chemical subspace is the multi‐component reaction (MCR). Apart from Domino reactions, MCR is one of the most promising routes for one‐pot synthesis. Thus, MCR derived product can be considered as a synthetic hub to a vast diversity of novel cyclic or acyclic compounds. Heterocyclic moiety such as naphthyridines, quinolines, dihydropyridines (DHPs), quinazolines, pyrimidines, imidazoles, diazepines, and spiro‐heterocycles are widely recognized in clinical evaluation. Because of their relevant significance, vast literature exists to accomplish the synthesis of these biologically important compounds. Therefore, this review highlights the last ten years of developments in the one‐pot synthesis of these heterocyclic moieties which are widely recognized by the industry in addition to academia.

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Section: Seven‐membered Heterocyclesmentioning

confidence: 99%

One‐Pot Multicomponent Reaction: A Highly Versatile Strategy for the Construction of Valuable Nitrogen‐Containing Heterocycles

et al. 2022

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“…To our knowledge, there are no example of sulfur nucleophiles involved in this type of cyclization. [6] Recent research of our group focused on the synthesis of medium-sized N,S-heterocycles, [7] which are poorly represented in the class of heterocyclic therapeutic agents, [8] with only three 7-membered ring representatives [9] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Access to 1,4‐Thiazepanes via Gold‐Catalyzed 7‐exo‐dig Thioallylation and their Cycloisomerization to Bicyclic [4.3.1] Bridgehead‐Olefinic Systems

et al. 2022

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A series of 1,4-thiazepanes were synthesized using gold-catalysis from 1,3-aminothioethers having two or three carbon stereocenters. The process consists in a 7-exo-dig cyclization with CÀ S bond formation and concomitant allyl S-to-C migration, which occurs intramolecularly as demonstrated by a cross-over experiment. X-ray crystal-structure analysis of one product confirmed the expected stereochemistry. Two examples of reactions, azide-alkyne cycloaddition (CuAAC) and N-alkylation, illustrate the potential postfunctionalization of the synthesized 1,4-thiazepanes. Finally, the N-propargyl 1,4-thiazepanes underwent a sulfur-assisted 1,6-enyne cycloisomerization, which led through a 6-exo-dig cyclization to N,Sheterobicyclo[4.3.1] systems with a bridgehead double bond.

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“…1,4-Thiazepines are important structural features for the design and synthesis of novel bioactive agents that exhibit prominent pharmacological activities . Actually, 1,4-thiazepines have been explored for years as an important class of heterocyclic compounds and still draw considerable attention as a result of the broad range of biological activities they possess, including antibacterial, anticonvulsant, antimicrobial, antioxidant, antipsychotic, and anticancer properties.…”

Section: Introductionmentioning

confidence: 99%

“…Notably, the most common examples of 1,4-thiazepines are comprised of half and fully saturated (i.e., dihydro, tetrahydro, and perhydro) benzo- and dibenzo-fused and/or oxo derivatives. Over the years, diverse methodologies have been disclosed for the synthesis of 1,4-thiazepines, , and new strategies continue to emerge since they are critical intermediates for the synthesis of many drugs and natural products. On the other hand, half and fully unsaturated monocyclic 1,4-thiazepines are far less known.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,4-Thiazepines

Kelgokmen

Zora

2018

J. Org. Chem.

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An efficient, general, and unprecedented methodology for the synthesis of 2-methylene-2,3-dihydro-1,4-thiazepines from N-propargylic β-enaminones is described. Initially, N-propargylic β-enaminones were thionated with Lawesson's reagent in good to high yields, and then the resulting N-propargylic β-enaminothiones were subjected to electrophilic cyclization. When treated with zinc chloride in refluxing chloroform, N-propargylic β-enaminothiones underwent electrophilic cyclization to yield 2-methylene-2,3-dihydro-1,4-thiazepines in good to high yields. A general trend was observed for all N-propargylic β-enaminothiones, and the cyclization proceeded with high efficiency and large functional group tolerance. This process is also applicable to the cyclization of internal alkyne-tethered N-propargylic β-enaminothiones. This operationally simple and facile method may represent a very rapid entry to a library of functionalized 1,4-thiazepines in the area of pharmaceuticals.

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1,4-Oxazepines and 1,4-Thiazepines

Cited by 10 publications

References 175 publications

One‐Pot Multicomponent Reaction: A Highly Versatile Strategy for the Construction of Valuable Nitrogen‐Containing Heterocycles

One‐Pot Multicomponent Reaction: A Highly Versatile Strategy for the Construction of Valuable Nitrogen‐Containing Heterocycles

Access to 1,4‐Thiazepanes via Gold‐Catalyzed 7‐exo‐dig Thioallylation and their Cycloisomerization to Bicyclic [4.3.1] Bridgehead‐Olefinic Systems

Synthesis of 1,4-Thiazepines

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