Syntheses and antifilarial profile of 7-chloro-4-(substituted amino) quinolines: a new class of antifilarial agents

Tewari, Swati; Chauhan, Prem M. S.; Bhaduri, A. P.; Fatima, Nishat; Chatterjee, R. K.

doi:10.1016/s0960-894x(00)00255-9

Cited by 55 publications

(23 citation statements)

References 11 publications

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“…Th e fi rst of the conventional mechanisms of the type SNHet is ipso-substitution of easily leaving groups and hydrogen [1,2]. Another variant of the substitutive functionalization on the principle of FGI are the transformations on arine mechanism (E, A) [3,4]. Finally, chronologically the last of the studied processes of substitution by nucleophiles is ANRORC -multistage process involving in the fi rst stage the disclosure of azine by nucleophile [5].…”

Section: Introductionmentioning

confidence: 99%

“…In fact, the disclosure of azines under the action of N-nucleophiles are not uncommon [6][7][8], however not all of these transformations culminate in the substitution of leaving group and reverse cyclization. In the present work we have given the results of the study of the main stages of the transformation of 4-alkyl-6-nitro-1,2,4-triazolo [5,1-c] [1,2,4]triazine-7-ones under the action of morpholine and the nature of substitution of the nitro group according to the ANRORC type was installed.…”

Section: Introductionmentioning

confidence: 99%

“…Previously, we described the reaction of 4-alkyl-6-nitro-1,2,4-triazolo [5,1-c] [1,2,4]triazine-7-ones in the substitution of the nitro group under the action of N-, O-, S -and C-nucleophiles [9], but the sequence of transformations remains obscure. In this study we investigated the features of substitution of nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c] [1,2,4] triazine-7-ones (1) containing methyl (1a) and tert-butyl fragments (1b) in the cycle triazine, creating a minimum and maximum steric eff ect to determine its eff ect on the reaction.…”

Section: Introductionmentioning

confidence: 99%

“…In this study we investigated the features of substitution of nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c] [1,2,4] triazine-7-ones (1) containing methyl (1a) and tert-butyl fragments (1b) in the cycle triazine, creating a minimum and maximum steric eff ect to determine its eff ect on the reaction.…”

Section: Introductionmentioning

confidence: 99%

“…The data of chromato-mass spectrometry of the reaction masses show the presence of the N-nitrosomorpholine, the product of substitution of the nitro group (3) and product of substitution of decarboxylation (4). Th e structure of 4-alkyl-6-morpholyl-1,2,4-triazolo [5,1-c] [1,2,4]triazine-7-ones (3) is set based on the data of 1 H NMR spectroscopy and elemental analysis (see experimental part).…”

Section: Introductionmentioning

confidence: 99%

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The features of nucleophilic substitution of the nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazines

et al. 2017

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The nucleophilic substitution of the nitro group of 4-alkyl-6-nitro-4,7-dihydro-1,2,4-triazolo[5,1-c][1,2,4]triazine-7-ones on the example of interaction with morpholine was studied. It is established that under the action of excess cycloalkylimine at room temperature the unusual easy disclosure of triazine cycle with the formation of sterically hindered hydrazones occurs which are the key intermediates for further transformations. The carrying of reaction at elevated temperatures leads to the formation of products of substitution of the nitro group with the amine and also with morpholyl hydrazones which are the products of hydrolysis of amides of hydrazones and subsequent decarboxylation. Thus, the nucleophilic substitution of the nitro group in the described triazolotriazines ows through the ANRORC mechanism.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

The features of nucleophilic substitution of the nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazines

et al. 2017

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Chemoselective Cyclodehydration of α‐Acyl‐β‐arylaminoacrylamides Using Hendrickson Reagent: Access to Polysubstituted 4‐Aminoquinolines and Diazaphenacenes

chitturi

Wang

et al. 2023

Adv Synth Catal

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A chemoselecive cyclodehydration of α-acyl-β-arylaminoacrylamides via an electrophilic activation strategy has been described. A series of substituted 4-aminopyridines are chemoselectively prepared in 73-92% yields from α-acyl-β-arylaminoacrylamides activated by hexaphenyloxodiphosphonium triflate (Hendrickson reagent), whereas substituted diaza[n]phenacenes (n = 4-6) are obtained in 72-93% yields directly from α-acyl-β-arylaminoacrylamides using Hendrickson reagent in combination with triflic anhydride (Tf 2 O). The synthetic protocols feature with readily available starting materials, mild reaction conditions, simple execution, and wide range of synthetic potential of products.

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ChemInform Abstract: Syntheses and Antifilarial Profile of 7‐Chloro‐4‐(substituted amino) Quinolines: A New Class of Antifilarial Agents.

et al. 2000

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Syntheses and antifilarial profile of 7-chloro-4-(substituted amino) quinolines: a new class of antifilarial agents

Cited by 55 publications

References 11 publications

The features of nucleophilic substitution of the nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazines

The features of nucleophilic substitution of the nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazines

Chemoselective Cyclodehydration of α‐Acyl‐β‐arylaminoacrylamides Using Hendrickson Reagent: Access to Polysubstituted 4‐Aminoquinolines and Diazaphenacenes

ChemInform Abstract: Syntheses and Antifilarial Profile of 7‐Chloro‐4‐(substituted amino) Quinolines: A New Class of Antifilarial Agents.

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