Efficient Synthesis of Some Novel Spiro Heterocycles Containing Thiazole, Oxazole, Thiadiazole and Triazolo-Thiadiazole Moiety Under Microwave Irradiation

Dabholkar, Vijay V.; Mishra, Sushil

doi:10.1515/hc.2006.12.3-4.241

Cited by 7 publications

(1 citation statement)

References 9 publications

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“…Substituent changes at the benzene ring of the compounds have shown different protective activity, which encouraged us to synthesize novel benzoxazole derivatives for fi nding new agents with higher biological activity. A variety of methods are available to synthesize benzoxazoles including coupling of aldehydes and carboxylic acids or their derivatives with 2-aminophenol in the presence of strong acids at high temperature, oxidative cyclization using manganese(IV) acetate, and a reaction of o -aminophenol and ethyl cyanoacetate in n -butanol with the benzoic acid catalysis (Varma and Kumar , 1998 ;Sridharan et al , 2005 ;Dabholkar and Mishra , 2006 ;Moghaddam et al , 2006 ;Han et al , 2009 ;Murty et al , 2010 ). Here, we report a convenient synthesis of a series of novel N -dichloroacetyl-2,3-dihydrobenzoxazole derivatives 3 with different substituents at the benzene ring by cycloaddition of 2-aminophenol ( 1 ) with dichloromethane followed by acylation of the resultant 2,3-dihydro-benzooxazole 2 with dichloroacetyl chloride.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of some novel N-dichloroacetyl-2,3-dihydrobenzoxazole derivatives

et al. 2011

Heterocyclic Communications

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A facile synthetic route was developed to N -dichloroacetyl-2,3-dihydrobenzoxazole derivatives 3 by cycloaddition of 2-amino-phenol ( 1 ) with dichloromethane and acylation of the resultant intermediate 2,3-dihydrobenzoxazole 2 with dichloroacetyl chloride. The structures of the compounds were characterized by IR, 1 H NMR, and 13 C NMR spectroscopy and elemental analysis. The preliminary biological tests showed that products 3 could protect maize against injury caused by acetochlor to some extent.

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Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of some novel N-dichloroacetyl-2,3-dihydrobenzoxazole derivatives

et al. 2011

Heterocyclic Communications

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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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Chapter 1 Dimedone: A Versatile Precursor for Annulated Heterocycles

Ashry

Awad

Kilany

et al. 2009

Advances in Heterocyclic Chemistry Volume 98

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Efficient Synthesis of Some Novel Spiro Heterocycles Containing Thiazole, Oxazole, Thiadiazole and Triazolo-Thiadiazole Moiety Under Microwave Irradiation

Abstract: 5,5-Dimethyl cyclohexane-l,3-dione 1 was treated with twice the molar quantity of bromine in glacial acetic acid to yield 2,2-dibromo-5,5-dimethyl cyclohexane-l,3-dione 2.

Cited by 7 publications

References 9 publications

Synthesis and biological activity of some novel N-dichloroacetyl-2,3-dihydrobenzoxazole derivatives

Synthesis and biological activity of some novel N-dichloroacetyl-2,3-dihydrobenzoxazole derivatives

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

Chapter 1 Dimedone: A Versatile Precursor for Annulated Heterocycles

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