343. Synthesis of some 1,2,4-triazines

Atkinson, C. M.; Cossey, H. D.

doi:10.1039/jr9620001805

Cited by 18 publications

(12 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As reported earlier (9), with unsymmetrical diketone a mixture of two possible isomers (10) is obtained. Thus the one pot synthesis of the title compound was achieved via the monoacyl hydrazone, which was generated in situ by the condensation of amides with 1, 2dicarbonyl compounds in presence of base.…”

supporting

confidence: 72%

Novel One Pot Synthesis of Substituted 1, 2, 4-Triazines

Nongkhlaw¹,

Myrboh²

2006

Heterocyclic Communications

View full text Add to dashboard Cite

Substituted-1, 2, 4-triazines were conveniently prepared in one pot by the condensation of amides and 1,2-diketones in presence of base, followed by cyclisation with hydrazine hydrate. Introduction1, 2, 4-triazines and their derivatives have been widely studied in terms of their synthetic methodologies and reactivity since some of these derivatives were reported to have promising biological activities (la-g). The synthesis of 1, 2, 4-triazines and their derivatives are well documented and their methods of preparations are manifold and varied. A survey of the literature revealed that 1, 2-dicarbonyl compounds (aliphatic, aromatic and aromatic-aliphatic) are the most common reagents used for the synthesis of I, 2, 4-triazines and their derivatives (2, 3). Laakso and coworkers (4), as well as other groups (5) reported the condensation of acylhydrazides with benzil in acetic acid containing ammonium acetate to give 5, 6-diphenyl-l, 2, 4-triazines with various aromatic and heterocyclic groups attached at position 3. A similar method was also applied by Metze and his group (6) and also Hasselquist (7) using a variety of aliphatic and aromatic 1, 2-diketones and aliphatic, aromatic, and heterocyclic acid hydrazides but with preliminary isolation of the 1, 2diketones monoacylhydrazones followed by ring closure with alcoholic ammonia under pressure to give substituted 1, 2, 4-triazines. Results and DiscussionsRecently, we have reported the synthesis of trisubstituted pyridazine by the condensation of 1, 2diketone with acetophenone in the presence of base, followed by cyclisation with hydrazine hydrate (8). We wish to report here the synthesis of 1, 2, 4-triazine starting from amides and 1, 2-dicarbonyl compounds and hydrazine hydrate in the presence of base.

show abstract

supporting

confidence: 72%

Novel One Pot Synthesis of Substituted 1, 2, 4-Triazines

Nongkhlaw¹,

Myrboh²

2006

Heterocyclic Communications

View full text Add to dashboard Cite

show abstract

“…shows the nine possible isomers of dihydro-1,2,4-triazine as well as three possible structures of the dihydro-1,2,4-triazinium cation. In the first preparative articles, the 2,5-dihydro (8) and the 4,5dihydro (9) isomers have been reported as reaction products[38,39]. In addition, UV spectroscopic measurements of 1,2,4-triazines with aryl substituents in the 3, 5 and 6-position of the heterocyclic ring indicate a tautomeric equilibrium between 8 and 9 in ethanol, consisting of predominantly 2,5-…”

mentioning

confidence: 99%

COSMO Implementation in TURBOMOLE: Extension of an efficient quantum chemical code towards liquid systems

Schäfer¹,

Klamt²,

Sattel³

et al. 2000

Phys. Chem. Chem. Phys.

672

615

View full text Add to dashboard Cite

The most recent algorithmic enhancements of the COSMO solvation model are presented and the implementation in the TURBOMOLE program package is described. Three demonstrative applications covering homogeneous catalysis, tautomeric equilibria, and binary phase diagrams show the efficiency and general applicability of the approach. Especially when combined with the COSMO-RS extension, the method very reliably predicts thermodynamic properties of liquid mixtures.

show abstract

“…Previously 5,6-diphenyl-3(3-and 4-pyridyl)-os-triazines have been prepared by the action of the corresponding acylhydrazine with• benzil and ammonia. [6][7] We have also prepared tetrakis(2-pyridyl)-3,3 '-bi (astriazine) (IV) by the action of oxamide dihydrazone, H2N-N=C(NH2)(NH2)C=N-NH2, on pyridyl. The preparation of hydrazidines of the formula RC-(=NH)NHNH2 has previously been accomplished by the action of hydrazine on the corresponding thio-amide2 or imido ether.3-4 Less commonly (as in the case of cyanothiazole4) they have been prepared by direct action of hydrazine on the nitrile.…”

Section: -Cyanopyridines1mentioning

confidence: 99%

The Preparation of Hydrazidines and as-Triazines Related to Substituted 2-Cyanopyridines¹

Case¹

1965

J. Org. Chem.

167

View full text Add to dashboard Cite

show abstract

343. Synthesis of some 1,2,4-triazines

Cited by 18 publications

References 0 publications

Novel One Pot Synthesis of Substituted 1, 2, 4-Triazines

Novel One Pot Synthesis of Substituted 1, 2, 4-Triazines

COSMO Implementation in TURBOMOLE: Extension of an efficient quantum chemical code towards liquid systems

The Preparation of Hydrazidines and as-Triazines Related to Substituted 2-Cyanopyridines¹

Contact Info

Product

Resources

About

343. Synthesis of some 1,2,4-triazines

Cited by 18 publications

References 0 publications

Novel One Pot Synthesis of Substituted 1, 2, 4-Triazines

Novel One Pot Synthesis of Substituted 1, 2, 4-Triazines

COSMO Implementation in TURBOMOLE: Extension of an efficient quantum chemical code towards liquid systems

The Preparation of Hydrazidines and as-Triazines Related to Substituted 2-Cyanopyridines1

Contact Info

Product

Resources

About

The Preparation of Hydrazidines and as-Triazines Related to Substituted 2-Cyanopyridines¹