cas 31602-66-1, 5-(1H-pyrrol-2-yl)-1H-tetrazole

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Just add tetrazole: 5-(2-Pyrrolo)tetrazoles are simple, highly potent anion recognition elements
We report a novel pyrrolo-tetrazole motif that encodes anion binding orders of magnitude stronger than closely related systems and suggests the general utility of amide-tetrazole exchanges for creating simple, high-affinity anion binders. The Royal Society of Chemistry 2011.
Courtemanche, Rebecca J. M.,Pinter, Thomas,Hof, Fraser
p. 12688 - 12690
(2011)
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Catalytic conversion of 2,4,5-trisubstituted imidazole and 5-substituted 1H-tetrazole derivatives using a new series of half-sandwich (η6-p-cymene)Ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazone ligands
A new series of half-sandwich (η6-p-cymene) ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazide derivatives [Ru(η6-p-cymene)(Cl)(L)] [L = N'-(naphthalen-1-ylmethylene)thiophene-2-carbohydrazide (L1), N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide (L2) and N'-(pyren-1-ylmethylene)thiophene-2-carbohydrazide (L3)] were synthesized. The ligand precursors and their Ru(II) complexes (1–3) were structurally characterized by spectral (IR, UV–Vis, NMR and mass spectrometry) and elemental analysis. The molecular structures of the ruthenium(II) complexes 1–3 were determined by single-crystal X-ray diffraction. All complexes were used as catalysts for the one-pot three-component syntheses of 2,4,5-trisubstitued imidazole and 5-substituted 1H-tetrazole derivatives. The catalytic studies optimized parameters as solvent, temperature and catalyst. The catalysts revealed very active for a broad range of aromatic aldehydes presenting either electron attractor or electron donor substituents and, although less active, moderate to high activities were observed for alkyl aldehydes.
Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Archana, Govindhasamy,Alves, Luis G.,Martins, Ana M.,Shanmuga Bharathi, Kuppannan
(2020/11/16)

Synthesis of 5-Substituted 1 H-Tetrazoles from Nitriles by Continuous Flow: Application to the Synthesis of Valsartan
An efficient continuous flow process for the synthesis of 5-substituted 1H-tetrazoles is described. The process involves the reaction between a polymer-supported triorganotin azide and organic nitriles. The polymer-supported organotin azide, which is in situ generated with a polystyrene-supported triorganotin alkoxide and trimethylsilylazide, is immobilized in a packed bed reactor. This approach is simple, fast (it takes from 7.5 to 15 min), and guarantees a low concentration of tin residues in the products (5 ppm). The process was developed to aryl-, heteroaryl-, and also alkylnitriles and was applied for the synthesis of valsartan, an angiotensin II receptor antagonist.
Carpentier, Florian,Felpin, Fran?ois-Xavier,Zammattio, Fran?oise,Le Grognec, Erwan
p. 752 - 761
(2020/03/13)

Antibacterial assessment of heteroaryl, Vinyl, Benzyl, and Alkyl tetrazole compounds
Background: In previous reports, the antibacterial properties of certain tetrazole derivatives have been described. We have previously reported the antibacterial properties of aryl 1H-tetrazole compounds. Objective: To study the antibacterial activity of 5-substituted heteroaryl, vinyl, benzyl, and alkyl 1H-tetrazole derivatives. Methods: The antibacterial properties of heteroaryl, vinyl, benzylic, and aliphatic tetrazole derivatives were investigated against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. The activity was assessed by determining the minimum inhibitory concentration of these tetrazole derivatives and comparing them to the known antibiotics amoxicillin, trimethoprim and sulfamethoxazole. Results: The tetrazole compounds were prepared utilizing cerium(III) chloride heptahydrate catalysis at 160o C for 1-4 h in a microwave reactor using an aqueous solvent mixture. The most active derivatives exhibited minimum inhibitory concentration values between 125-250 μg/mL against Escherichia coli. More importantly, these compounds were considerably more active when used in combination with trimethoprim and a significant synergistic effect was observed (MIC = 0.98-7.81 μg/mL) against E. coli and S. aureus. Conclusion: The tetrazole derivatives were synthesized in high yield and short reaction times in water. Several of the tetrazole compounds showed a significant synergistic antibacterial effect when used with trimethoprim.
Dudley, Joshua,Feinn, Liana,Defrancesco, Heather,Lindsay, Erica,Coca, Adiel,Roberts, Elizabeth Lewis
p. 550 - 555
(2018/08/17)

A Practical Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Employing the Azide Anion from Diphenyl Phosphorazidate
5-Substituted 1 H -tetrazoles were effectively synthesized from aldoximes and diphenyl phosphorazidate (DPPA) under reflux conditions in xylenes. Various aldoximes underwent the cycloaddition reaction to afford the corresponding 5-substituted 1 H -tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.
Ishihara, Kotaro,Kawashima, Mayumi,Matsumoto, Takatoshi,Shioiri, Takayuki,Matsugi, Masato
p. 1293 - 1300
(2017/12/26)

Development and Demonstration of a Safer Protocol for the Synthesis of 5-Aryltetrazoles from Aryl Nitriles
The search for a faster, safer protocol for the direct synthesis of 5-aryltetrazoles from aryl nitriles in the presence of sodium azide and an amine hydrochloride salt led to the discovery of a buffered system comprised of BnNH2, BnNH2·HCl, and NaN3. After optimization of reaction conditions and a thorough investigation of reaction safety, the procedure was demonstrated for the synthesis of several hundred grams of 4-chloro-2-(2H-tetrazol-5-yl)phenol. The generality of the developed reaction conditions was established by a small-scale reactivity screen using 16 additional aryl and heteroaryl nitrile substrates.
Treitler, Daniel S.,Leung, Simon,Lindrud, Mark
p. 460 - 467
(2017/03/24)

Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Using Diphenyl Phosphorazidate
A novel method for the synthesis of 5-substituted 1H-tetrazoles using diphenyl phosphorazidate (DPPA) has been developed. Aromatic and aliphatic aldoximes underwent cycloaddition to afford the corresponding 5-substituted 1H-tetrazoles with ease and efficiency.
Ishihara, Kotaro,Kawashima, Mayumi,Shioiri, Takayuki,Matsugi, Masato
supporting information
p. 2225 - 2228
(2016/11/06)

PHENYL-3-{ (3- (1H- PYRROL- 2 -YL) - [1 , 2 , 4] 0XADIAZ0L-5-YL] PIPERIDIN-1-YL}-METHANONE DERIVATIVES AND RELATED COMPOUNDS AS POSITIVE ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
The present invention provides new compounds of formula (I) as positive allosteric modulators of metabotropic receptors - subtype 5 ("mGluR5") which are useful for the treatment or prevention of central nervous system disorders such as for example, cognitive decline, both positive and negative symptoms in schizophrenia as well as other central or peripheral nervous system disorders in which the mGluR5 subtype of glutamate metabotropic receptor is involved. The invention is also directed to pharmaceutical compounds and compositions in the prevention or treatment of such diseases in which mGluKi is involved. W represents (C4-C7)cycloalkyl, (C3-C7)heterocycloalkyl , (C3-C7)heterocycloalkyl-(C1-C3)alkyl or (C3-C7)heterocycloalkenyl ring; represents a (C5-C7)heteroeycloalkyl, (C5-C7)heterocycloalkeiiyl ring or a heteroaryl group of formula (a), (b), (c), (d), (e), (f), (g), (i). Q denotes a cycloalkyl, an aryl or heteroaryl group of formula (j), (k), (l), (m), (n). A is azo -N=N-, ethyl, ethenyl, ethynyl, -NR8C(=O)-, -NR8C(=O)-O-, -NR8C(=O)-NR9, NR8S(=O)2-, -C(=O)NR8-, -O-C(=O)NR8-, -S-, -S(=O)-, -S(=O)2-, -S(C=O)2NR8-, -C(=0)-0-, -0-C(=0)-, -C(=NR8)NR9-, C(C=NOR8)NR9- , -NR8C(=NOR9)-, =N-0-, -0-N=CH- or a group aryl or heteroaryl of formula, (o), (p), (q), (r), (s), (t), (u), (v), (w), (x). The other substituents are defined in the claims.
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Page/Page column 75

(2008/06/13)

Synthesis of new tetrazole-substituted pyroaminoadipic and pipecolic acid derivatives
Racemic 5-aryl- and 5-(arylmethyl)tetrazolyl-substituted pyroaminoadipic and pipecolic acid derivatives were diastereoselectively synthesized from dimethyl meso-2,5-dibromoadipate (1) in good yields under mild reaction conditions. The key step of this reaction sequence is the selective N2-alkylation of 5-substituted tetrazoles with 1. The reactive 2-bromo-5-tetrazolyladipate derivatives 2a-g were generated and treated with sodium azide, followed by Pd/C-catalyzed hydrogenation, to provide lactams 4a-g. The chemoselective reduction of the amide carbonyl group of 4a-g with BH 3, followed by acid hydrolysis, provided 5-tetrazolylpipecolic acids in racemic form. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Lenda, Fatimazohra,Guenoun, Farhate,Tazi, Bouchra,Iarbi, Najib Ben,Allouchi, Hassan,Martinez, Jean,Lamaty, Frederic
p. 326 - 333
(2007/10/03)

The use of 5-substituted tetrazoles in a synthesis of heterocyclic α-amino esters
A general method of synthesis of γ-tetrazolyl α-amino esters by selective N(2)-alkylation of 5-substituted tetrazoles with halogeno derivatives of homoserine is reported.
Alami, A.,Hallaoui, A. El,Elachqar, A.,Roumestant, M. L.,Viallefont, Ph.
p. 769 - 772
(2007/10/03)

Chemical Properties

Melting Point: 224-226 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
Boiling Point: 430.957 °C at 760 mmHg
Flash Point:225.636 °C
Density: 1.484 g/cm³
Refractive Index: 1.669
PKA: 4.94±0.10(Predicted)
PSA: 70.25000
LogP: 0.19480

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31602-66-1

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Chemical Properties

Melting Point: 224-226 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))

Boiling Point: 430.957 °C at 760 mmHg

Flash Point:225.636 °C

Density: 1.484 g/cm³

Refractive Index: 1.669

PKA: 4.94±0.10(Predicted)

PSA: 70.25000

LogP: 0.19480

Global suppliers and manufacturers of 31602-66-1total 15 suppliers on LookChem

Article Database

31602-66-1

Articles about 31602-66-1Total 10 be found

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Chemical Properties

Melting Point: 224-226 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))

Boiling Point: 430.957 °C at 760 mmHg

Flash Point:225.636 °C

Density: 1.484 g/cm3

Refractive Index: 1.669

PKA: 4.94±0.10(Predicted)

PSA: 70.25000

LogP: 0.19480

Global suppliers and manufacturers of 31602-66-1total 15 suppliers on LookChem

Density: 1.484 g/cm³