ChemInform Abstract: Synthesis of 5H‐Quino(3,4‐b)(1,4)benzothiazin‐6(12H)‐ones.

Anireddy, Jaya Shree; Rao, V. S.; Darbarwar, M.

doi:10.1002/chin.199042233

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“…1,5‐Benzoheteroazepines are nitrogen‐ and sulfur‐containing seven‐membered heterocyclic compounds that exhibit a broad range of interesting biological activities, and numerous drug molecules have been developed based on 1,5‐benzothiazepines (Scheme ). For example, 1,5‐benzothiazepine‐based compounds have been reported to exhibit Ca 2+ channel antagonistic activity, CNS depressant activity, antiplatelet aggregator activity, anticancer activity, anti ‐HIV activity, antimicrobial activity, cardiovascular activity, and cholinesterase inhibitory activity . 1,5‐Benzodiazepines (seven‐membered heterocyclic compounds containing two nitrogen atoms) are widely used as anticonvulsant, anti‐anxiety, sedative, and antidepressants .…”

Section: Introductionmentioning

confidence: 99%

Sustainable Catalytic Process with a High Eco‐Scale Score for the Synthesis of Five‐, Six‐, and Seven‐Membered Heterocyclic Compounds Using Nanocrystalline Zeolites

Sarmah

Srivastava

2017

Asian J Org Chem

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Nanocrystalline ZSM-5 and Beta zeolites were evaluated as catalysts for the one-pot synthesis of aw ide range of five-, six-, and seven-memberedh eterocyclic compounds. Seven-membered compounds were prepared by the reaction of o-phenylenediamine and ketones, whereas five-membered compounds were obtained when o-aminothiophenol was reactedw ith ketones under the same reactionc ondition. Severalo ther seven-membered compounds werep repared by the reaction of (E)-chalcone with o-phenylenediamine/o-aminothiophenol, whereas the six-membered compounds described in this study were prepared by the reaction of o-phenylenediamine with 2-bromoacetophenone/2hydroxy acetophenone. Twoo ther five-membered compounds were prepared by the reactiono fa niline with ben-zaldehyde and thioglycolic acid, and the reaction of glycerol with acetone. The mechanisms responsible for the formation of the different products were elucidated based on the results of time-dependent 1 HNMR experiments.T ot he best of our knowledge, this work represents the first reported systematicassessment of the catalytic activity of nanocrystalline zeolites for the synthesis of heterocyclic compounds. Notably,t he catalysts were readily recovered and reused without any considerable decrease in their catalytic activity.T he high eco-scale score and low E-factorv alue of this process clearly demonstrate that it represents ag reen and sustainable synthetic route for the preparation of aw ide range of heterocyclic compoundso fs ignificant industrial importance.Scheme1.Some representative examples of biologically important molecules containingf ive-, six-, and seven-membered heterocyclicunits.Scheme2.Various pathways for the construction of five-membered heterocyclic compoundsreported in the literature.

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