A novel, facile, simple and convenient oxidative aromatization of Hantzsch 1,4‐dihydropyridines to pyridines using polymeric iodosobenzene with KBr

Kumar, Parvin

doi:10.1002/jhet.504

Cited by 16 publications

(8 citation statements)

References 54 publications

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“…Encouraged by these observation and in continuation of our earlier studies on the oxidative aromatization of 1,4-DHP,s [39][40][41][42] and synthesis of biological active heterocyclic compounds [52][53] , we report herein, solvent free aromatization of diethyl 2, …”

Section: Introductionmentioning

confidence: 55%

Solvent-free synthesis and oxidative aromatization of diethyl-2,6-dimethyl-4-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylates using hypervalent iodine (III) reagents

Kumar¹,

Hussain²,

Kumar³

2014

10.5267/j.ccl

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In this article, an efficient, environmentally benign, solvent-free synthesis of diethyl-2,6-dimethyl-4-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylates and their simple oxidative aromatization in presence of selected hypervalent iodine (III) reagents under solvent-free condition at room temperature is demonstrated. All reactions were carried out by grinding the reactant pyrazole substituted Hantzch-1,4-dihydropyridines and hypervalent iodine (III) reagent in a mortar with pestle. [Hydroxy(tosyloxy)iodo]benzene act as an more efficient oxidizing reagent in comparison to phenyliodine bistrifluoroacetate and iodobenzene diacetate in terms of reaction time and yields. The advantages of present protocol are the environment friendly, short reaction time, mild reaction conditions, and high yields of the products.

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Section: Introductionmentioning

confidence: 55%

Solvent-free synthesis and oxidative aromatization of diethyl-2,6-dimethyl-4-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylates using hypervalent iodine (III) reagents

Kumar¹,

Hussain²,

Kumar³

2014

10.5267/j.ccl

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“…In continuation on the synthesis of biologically active heterocycles and our ongoing attention to the development of new methodologies [42, 43], herein we describe the solvent‐free oxidative condensation of 2‐aminothiophenol and 2‐aryl/heteroaryl aldehydes using hypervalent iodine (III) reagents. The high oxidizing power of IBD and PIFA led us to hypothesize that these can act as efficient oxidizing reagents for this protocol (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Solvent‐Free One Pot Synthesis of 2‐aryl/Heteroarylbenzothiazoles Using Hypervalent Iodine (III) Reagents

Kumar

Meenakshi

Kumar

et al. 2012

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).In this article, an efficient, environmentally benign, one-pot and simple synthesis of 2-aryl/heteroarylbenzothiazoles by the reaction of 2-aminothiophenol and aryl/heteroaryl aldehydes mediated by hypervalent iodine (III) reagents under solvent-free condition at room temperature is demonstrated. All the reactions were carried out by grinding the reactants (2-aminothiophenol and aryl/heteroaryl aldehydes) with hypervalent iodine (III) reagents in a mortar with pestle. Phenyliodine bistrifluoroacetate act as an efficient oxidizing reagent in comparison to iodobenzene diacetate in term of reaction time but yields are comparative. The advantages of this protocol are the one-step procedure, mild reaction conditions, high yields of the products, and no side reactions. CDCl 3 ): δ 3.87 (s, 3H), 6.98-7.02 (m, 2H), 7.30-7.36 (m, 2H), 7.44-7.50 (m, 3H), 7.67-7.69 (m, 2H), 7.76-7.78 (m, 1H), 7.81-7.83 (m, 2H), 8.02 (d, J = 8.0 Hz, 1H), 8.66 (s, 1H). Anal. Calcd. for C 23 H

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“…It brings advantages from the environmental point of view, as well as rate enhancement, less waste products, and higher yields [32]. In continuation of our previous work [16,[33][34][35][36][37] on biologically active heterocyclic compounds and development of novel synthetic methodologies and because of the biological significance of 1,2,4-triazole, a solvent-free oxidative cyclization of 2-pyridyl-and 2-quinolylhydrazones with phenyliodine bis(trifluoroacetate) (PIFA) or iodobenzene diacetate (IBD) to the corresponding 3-aryl-[1,2,4]triazolo[4,3-a]pyridines and 1-aryl-5-methyl-[1,2,4]triazolo[4,3-a]quinolines is reported here.…”

mentioning

confidence: 82%

An environmentally benign and solvent-free synthesis of 3-aryl[1,2,4]triazolo[4,3-a]pyridines and 1-aryl-5-methyl[1,2,4]triazolo[4,3-a]quinolines using phenyliodine bis(trifluoroacetate) or iodobenzene diacetate

Kumar

2012

Chem Heterocycl Comp

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A novel, facile, simple and convenient oxidative aromatization of Hantzsch 1,4‐dihydropyridines to pyridines using polymeric iodosobenzene with KBr

Cited by 16 publications

References 54 publications

Solvent-free synthesis and oxidative aromatization of diethyl-2,6-dimethyl-4-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylates using hypervalent iodine (III) reagents

Solvent-free synthesis and oxidative aromatization of diethyl-2,6-dimethyl-4-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylates using hypervalent iodine (III) reagents

Solvent‐Free One Pot Synthesis of 2‐aryl/Heteroarylbenzothiazoles Using Hypervalent Iodine (III) Reagents

An environmentally benign and solvent-free synthesis of 3-aryl[1,2,4]triazolo[4,3-a]pyridines and 1-aryl-5-methyl[1,2,4]triazolo[4,3-a]quinolines using phenyliodine bis(trifluoroacetate) or iodobenzene diacetate

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