Herbicidal activity and redox properties of 3-aryl-6-(perfluoroalkyl)-1,2,4,5-tetrazines and 1,2-dihydro derivatives

Pilgram, K.; Wittsell, Lawrence; Skiles, Richard D.; James, Allan L.; Dawson, Jane

doi:10.1021/jf60212a021

Cited by 6 publications

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“…1). [16][17][18][19] Among many reported 1,2,4,5-tetrazine derivatives, 20 the 3,6symmetrically disubstituted ones are common due to their synthetic accessibility. 1b,13,21 In contrast, the reported 3,6unsymmetrically disubstituted-1,2,4,5-tetrazines are limited, and especially their substituents at C3 and C6 positions are usually the alkyl and some specic substituent groups (methylthio, methoxycarbonyl and methylsulnyl).…”

Section: Introductionmentioning

confidence: 99%

Novel 3,6-unsymmetrically disubstituted-1,2,4,5-tetrazines: S-induced one-pot synthesis, properties and theoretical study

Yin

et al. 2015

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

Novel 3,6-unsymmetrically disubstituted-1,2,4,5-tetrazines: S-induced one-pot synthesis, properties and theoretical study

Yin

et al. 2015

RSC Adv.

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Conformation and bonding in unsymmetrically 3,6‐disubstituted dihydro‐1,2,4,5‐tetrazine

Pilgram

Gale

Skiles

1985

Journal of Heterocyclic Chem

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The molecular structure of the title compound, I, has been determined by single‐crystal X‐ray diffraction. The crystals are triclinic, space group PI. The analysis revealed that the dihydro‐s‐tetrazine molecule is in a slightly twisted boat conformation with the nitrogen atoms carrying the two hydrogens, N(2) and N(4), pointing upward. All substituents on the dihydro‐s‐tetrazine ring exist in pseudo‐equatorial configurations. Adjacent hydrogen and bulky groups (CF3 and p‐Cl‐C6H4) have cis‐relationships. The p‐chlorophenyl group is twisted with respect to the dihydro‐s‐tetrazine ring. The unit cell for I contains six molecules. Each dihydro‐s‐tetrazine ring participates in four intermolecular hydrogen bonds (N···H bond distance 2.23 to 2.41 A), two hydrogen bonds to each adjacent tetrazine ring in the same unit cell.

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Ring closures with α‐chloroazines

Pilgram

Skiles

1987

Journal of Heterocyclic Chem

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Two series of unsymmetrical 3,6‐disubstituted 1,2,3,4‐tetrahydro‐1,2,4,5‐tetrazines and 3,5‐disubstituted 4‐amino‐2,3‐dihydro‐1,2,4‐triazoles were synthesized from unsymmetrical 1,4‐disubstituted 1‐chloroazines with hydrazine, 1‐methylhydrazine, and 1,2‐dimethylhydrazine. These partially reduced heterocycles belong to little known and less accessible classes of heterocycles.

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Herbicidal activity and redox properties of 3-aryl-6-(perfluoroalkyl)-1,2,4,5-tetrazines and 1,2-dihydro derivatives

Cited by 6 publications

References 11 publications

Novel 3,6-unsymmetrically disubstituted-1,2,4,5-tetrazines: S-induced one-pot synthesis, properties and theoretical study

Novel 3,6-unsymmetrically disubstituted-1,2,4,5-tetrazines: S-induced one-pot synthesis, properties and theoretical study

Conformation and bonding in unsymmetrically 3,6‐disubstituted dihydro‐1,2,4,5‐tetrazine

Ring closures with α‐chloroazines

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