Synthesis and properties of phenylenebis-1H-tetrazoles

Гапоник, П. Н.; Karavai, V. P.; Davshko, I. E.; Degtyarik, Mikhail M.; Bogatikov, A. N.

doi:10.1007/bf00476984

Cited by 14 publications

(16 citation statements)

References 3 publications

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“…8.14 (both d,1 H each,J = 8.1 Hz);8.25,9.95,10.15 (all s,1 H each). 13 C NMR (DMSO d 6 ), δ: 17.1 (CH 3 ); 119.0 (=CH); 122.8 (=CH); 132.3 (=C); 133.1 (=CH); 133.6 (=C); 134.9 (=C); 142.3 (=CH); 144.6 (=CH).…”

Section: Methodsmentioning

confidence: 99%

“…90-8.40 (m, 3 H); 8.12 (s, 1 H). 13 1,3 Bis(tetrazol 5 yl)benzene (5). A round bottom flask fit ted with a reflux condenser was charged with isophthalonitrile (0.71 g, 5.5 mmol), sodium azide (0.75 g, 13 mmol), NH 4 Cl (0.68 g, 13 mmol), and DMF (5 mL).…”

Section: Methodsmentioning

confidence: 99%

“…12 Bis(tetrazol 1 yl)benzenes 1 and 4 and 1 phenyltetrazole (6) were prepared according to a known procedure. 13 4 Methyl 1,3 bis(tetrazol 1 yl)benzene (2). A round bottom flask fitted with a reflux condenser was charged with sodium azide (2.27 g, 35 mmol), a solution of triethyl orthoformate (4.87 g, 33 mmol) in glacial acetic acid (20 mL), and 2,4 di aminotoluene (1.3 g, 11 mmol) and the mixture was refluxed with stirring for 6 h. The mixture was then cooled and diluted with water (50 mL).…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?

Burukin

Васильев

Merkulova³

et al. 2006

Russ Chem Bull

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show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?

Burukin

Васильев

Merkulova³

et al. 2006

Russ Chem Bull

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show abstract

“…The cyanamides 2a-m were reported and fully characterized by spectroscopic methods. [22][23][24][25][26][27][28][29][30][31][32] For example, compound 2k possessed characteristic peak at 123.72 ppm, which represented the 13 C in NH-C"N. The IR absorptions of 2k showed peaks at 2226 cm À1 for stretching of the -C"N group and at 3365 cm À1 for stretching of the -NH group.…”

Section: Introductionmentioning

confidence: 99%

Desulfurization and transformation of isothiocyanates to cyanamides by using sodium bis(trimethylsilyl)amide

Chen

Wong

Huang

et al. 2008

Tetrahedron Letters

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“…More recently, an efficient method for the synthesis of 1-aryltetrazoles has been proposed [21]. The latter compounds produce N-arylcyanamides when treated with KOH in DMSO [22,23].…”

mentioning

confidence: 99%

Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane

Butkevich

Zibinsky

Соколов

et al. 2012

Chem Heterocycl Comp

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Alkylation of N-arylcyanamides with (chloromethyl)thiirane in aqueous alkaline solution provides an easy synthetic approach to N-aryl-N-(thietan-3-yl)cyanamides. Yields vary from 34 to 76% and are lower in the case of electron-deficient aryl substituents. The reaction with phenols containing electronwithdrawing groups results in formation of 3-(aryloxy)thietanes in 19-45% yields.Small molecules comprise a vast majority of successfully designed, tested, and clinically approved drugs [1,2]. Structure-activity relationship practices used in early steps of the molecular design call for a large variety of substituents that one should be able to install onto the desired scaffold for the screening purposes. Therefore, simple and selective methods for the functionalization of organic molecules (as can be illustrated by examples of O-alkylation of phenols and N-acylation and N-sulfonylation of amines) play an important role whenever it is necessary to quickly achieve high molecular diversity or optimize the substrate-target interaction by varying the substitution pattern of the substrate. The absence of transition metal catalyst in such reactions is an additional advantage if bioactivity tests are in view.Small-ring heterocycles provide an attractive extension to the small alkyl and cycloalkyl set of substituents, as the presence of a heteroatom allows for an additional hydrogen bonding or dipole interactions between the substrate molecule and its target. Three-membered heterocycles, such as oxirane or aziridine fragments, often introduce unwanted reactivity because of the possibility of ring-opening reactions resulting in formation of electrophilic species. Four-membered heterocyclic fragments containing one heteroatom are inherently stable but notoriously difficult to synthesize. In this work, a simple and versatile method of introduction of 3-thietanyl substituent is discussed.

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Synthesis and properties of phenylenebis-1H-tetrazoles

Cited by 14 publications

References 3 publications

Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?

Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?

Desulfurization and transformation of isothiocyanates to cyanamides by using sodium bis(trimethylsilyl)amide

Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane

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