Synthesis of NewN-(4-Pyridyl)-1-aminopyrazoles and Their Muscarinic and Adrenergic Properties

Rodríguez‐Franco, María Isabel; Dorronsoro, Isabel; Martı́nez, Ana; Pérez, Concepción; Badı́a, Albert; ̃os, Josep E. Ban

doi:10.1002/(sici)1521-4184(20005)333:5<118::aid-ardp118>3.0.co;2-q

Cited by 15 publications

(6 citation statements)

References 19 publications

(18 reference statements)

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“…Recently, we reported some applications of heteroarylthioureas as versatile intermediates in the synthesis of new heterocyclic systems of biological interest [9][10][11][12][13]. Combining the above results with our work on heterocyclic derivatives of 4-aminopyridine (I) with cholinergic and adrenergic properties [14,15], here we report new pyridyl thioureas and ureas (II), as well as new thiazolines (III) derived from the same starting thioureas (Figure 1).…”

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confidence: 63%

Studies on the reactivity of some N‐aryl‐ and N‐heteroaryl‐N'‐alkylthioureas towards electrophilic reagents. Synthesis of new N‐pyridylthioureas and thiazolines maría

Rodriguez‐Franco

Dorronsoro

and

et al. 2001

Journal of Heterocyclic Chem

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Here in we describe our findings about the behaviour of some N-aryl-and N-heteroaryl-N'-alkylthioureas towards electrophilic reagents. In acid medium, the treatment of thioureas bearing aryl groups with 4-chloropyridine in 2-propanol yielded N-aryl-N-(4-pyridyl)-N'-alkylthioureas and N-aryl-N'-alkylureas, whereas the heteroarylthioureas tested under similar reaction conditions afforded N-heteroaryl-N'-alkyl-O-(2-propyl)isoureas. The reaction of N- (5,6,7,8-tetrahydronaphth-1-yl)-and N-(2-benzimidazolyl)-N'-butylthiourea with propargyl bromide in acid medium led to the formation of 2-butylimino-3-arylthiazolines, in a regioselective way. However, when this reaction was carried out in basic conditions the regioselectivity failed and a mixture of isomeric thiazolines was obtained. The Z-or E-configuration of the imino group of the synthesized thiazolines was studied by molecular modelling and by selective nuclear Overhauser experiments in nuclear magnetic resonance.

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supporting

confidence: 63%

Studies on the reactivity of some N‐aryl‐ and N‐heteroaryl‐N'‐alkylthioureas towards electrophilic reagents. Synthesis of new N‐pyridylthioureas and thiazolines maría

Rodriguez‐Franco

Dorronsoro

and

et al. 2001

Journal of Heterocyclic Chem

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“…The diester 40 and its ethyl analog are well known compounds [27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43]. The X-ray structure of the diethyl 1H-pyrazole-3,5-dicarboxylate has been determined [44].…”

Section: Discussion Of the Tablesmentioning

confidence: 99%

A Theoretical Study on the Tautomerism of C-Carboxylic and Methoxycarbonyl Substituted Azoles

Alkorta

Elguero

2005

Struct Chem

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DFT calculations (B3LYP/6-31+G * * ) have been carried out on 106 tautomers and conformers of NH-azoles bearing CO 2 H and CO 2 CH 3 groups. The following azoles systems have been studied: 2-substituted pyrroles, 2-substituted indoles, 2-substituted imidazoles, 2-substituted benzimidazoles, 4(5)-substituted imidazoles, 3(5)-substituted pyrazoles, 3-substituted indazoles (1H and 2H), 3,4(5)-substituted-1,2,3(5)-triazoles, 2,3(5)-substituted-1,2(3),4-triazoles, 4(5)-1,2,3,4(5)-tetrazoles. In the case of pyrazole, 3,5-disubstituted derivatives have also been computed, including four dimers.

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“…NMR spectra were recorded in CDCl 3 solutions, using Varian Unity-500 and Varian XL-300 spectrometers. Typical spectral parameters for 1 H NMR were: spectral width 10 ppm, pulse width 9 ms (57°), data size 32 K. The acquisition parameters in decoupled 13…”

Section: Methodsmentioning

confidence: 99%

“…In continuation of our work on the cholinergic agents of potential application in Alzheimer's disease, that either activate the neurotransmitter receptors (e.g. postsynaptic M 1 muscarinic agonists 13 ) or increase acetylcholine level in the synaptic cleft (AChE inhibitors 14 ), we are now interested in the synthesis of new compounds derived from N-benzylpiperidine and purines as potential acetylcholinesterase inhibitors (Figure).…”

mentioning

confidence: 99%

1-Benzyl-4-chloromethylpiperidine: A Building Block in the Synthesis of Compounds of Pharmacological Interest

Rodríguez‐Franco¹,

Fernández‐Bachiller²

2002

Synthesis

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The first synthesis of 1-benzyl-4-(chloromethyl)piperidine (1) is described, together with its application in the synthesis of potential pharmaceuticals. Reaction of 1 with several purines in basic medium proceed through the initial formation of 1-benzyl-1azoniabicyclo[2.2.1]heptane system, which then undergoes nucleophilic attack at two different carbons, yielding N-benzylpiperidine and N-benzylpyrrolidine derivatives.

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Synthesis of NewN-(4-Pyridyl)-1-aminopyrazoles and Their Muscarinic and Adrenergic Properties

Cited by 15 publications

References 19 publications

Studies on the reactivity of some N‐aryl‐ and N‐heteroaryl‐N'‐alkylthioureas towards electrophilic reagents. Synthesis of new N‐pyridylthioureas and thiazolines maría

Studies on the reactivity of some N‐aryl‐ and N‐heteroaryl‐N'‐alkylthioureas towards electrophilic reagents. Synthesis of new N‐pyridylthioureas and thiazolines maría

A Theoretical Study on the Tautomerism of C-Carboxylic and Methoxycarbonyl Substituted Azoles

1-Benzyl-4-chloromethylpiperidine: A Building Block in the Synthesis of Compounds of Pharmacological Interest

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