Recent Advances in the Chemistry of as-Triazinuum Salts

Чупахин, О. Н.; Чупахин, О. Н.; Alexeev, S. G.; Rudakov, B. V.; Charushin, Valery N.

doi:10.3987/rev-91-sr1

Cited by 29 publications

(15 citation statements)

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“…The chemistry of 1,2,4-triazines 82 has been reviewed at numerous occasions 10,[102][103][104][105] . There exists a considerable similarity between the chemical properties of 1,2,4-triazines 82 and quinazolines 65 -particularly in their reactivity in addition and elimination reactions 106,107 .…”

Section: Reactions Of 124-triazinesmentioning

confidence: 99%

Additions of water, hydroxide ions, alcohols and alkoxide ions to carbonyl and azomethine bonds

Zuman¹

2002

Arkivoc

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In this review are discussed equilibria involved in nucleophilic additions of H 2 O, HO -, ROH, and RO -(where R is an alkyl) to compounds containing carbonyl and azomethine bonds. These reactions result in a formation of covalent bonds between the heteroatom of the nucleophile and the carbon of the carbonyl double bond. After a brief summary of reactions resulting in additions to aliphatic carbonyl compounds, attention is paid to additions to benzaldehydes and formyl aromatic heterocycles. Equilibria involving additions to pyridoxal and some related compounds are dealt with in some detail. Discussion of additions of stated nucleophiles to azomethine bonds is practically restricted to additions to C=N bonds in heterocyclic rings. The reactivity of nucleophiles in such additions depends on the number of heteroatoms (in particular nitrogen) in the attacked ring, as well as on the number and position of substituents in such rings. In polynuclear compounds the reactivity depends on the number and kind of annelled rings, on the number and mutual position of heteroatoms and on the kind, number and position of substituents. In particular additions to pyrimidines, quinazolines, 1,2,4-and 1,3,5-triazines, pteridines and other heterocycles with four nitrogens, as well as 8-azapurines are mentioned.

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Section: Reactions Of 124-triazinesmentioning

confidence: 99%

Additions of water, hydroxide ions, alcohols and alkoxide ions to carbonyl and azomethine bonds

Zuman¹

2002

Arkivoc

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“…In the course of these studies we have established that the 1,2,4-triazine ring is prone to undergo diaddition reactions with bifunctional nucleophiles at C-5 and C-6 leading to the formation of condensed triazines [6,8,10,11].…”

Section: Introductionmentioning

confidence: 99%

“…Some nucleophiles have been found to react with N-protonated 1,2,4-triazines [10], however acidic conditions are not always acceptable, since protonation of nucleophilic species may also take place. This can be avoided by using other types of charged triazines, in particular quaternary Nalkyl-1,2,4-triazinium salts [2,5,6,10,13]. Three isomeric N-alkyl-1,2,4-triazinium salts can plausibly be derived from N-alkylation of 1,2,4-triazines [6].…”

Section: Introductionmentioning

confidence: 99%

“…This can be avoided by using other types of charged triazines, in particular quaternary Nalkyl-1,2,4-triazinium salts [2,5,6,10,13]. Three isomeric N-alkyl-1,2,4-triazinium salts can plausibly be derived from N-alkylation of 1,2,4-triazines [6]. Previous studies have shown that the N 1 -alkyl quaternary salts are formed predominantly, when 1,2,4-triazines react with trialkyloxonium tetrafluoroborates [6,13,14].…”

Section: Introductionmentioning

confidence: 99%

“…In previous papers we described new possibilities to modify the structure of 1,2,4-triazines by using the S N Hreactions and other related processes based on nucleophilic mono-or diaddition reactions at unsubstituted carbons of the triazine ring [5][6][7][8][9][10][11]. In the course of these studies we have established that the 1,2,4-triazine ring is prone to undergo diaddition reactions with bifunctional nucleophiles at C-5 and C-6 leading to the formation of condensed triazines [6,8,10,11].…”

Section: Introductionmentioning

confidence: 99%

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A simple one pot synthesis of condensed 1,2,4‐triazines by using the tandem a_N‐S_N^ipso and S_N^H‐S_N^ipsa reactions

Чупахин¹,

Rusinov²,

Beresnev³

et al. 2001

Journal of Heterocyclic Chem

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A new synthetic approach to condensed 1,2,4-triazines based on using the tandem A N -S N ipso and S N H -S N ipso reactions has been developed. 5-Methoxy-3-penyl-1,2,4-triazine and its N 1 -methyl quaternary salt were found to react with C,N-, C,O-and N,N'-bifunctional nucleophiles (m-phenylenediamine, resorcinol, semicarbazide and ureas) into triazacarbazoles, benzofuro[2,3-e][1,2,4]-triazines, and 6-azapurine derivatives. In all cases nucleophiles attack first the unsubstituted C-6 carbon of the triazine ring, while the final stage is replacement of the methoxy group affording cyclization products.

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Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Oliva¹,

Laza²,

Ocáriz³

2011

Modern Heterocyclic Chemistry

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Recent Advances in the Chemistry of as-Triazinuum Salts

Cited by 29 publications

References 1 publication

Additions of water, hydroxide ions, alcohols and alkoxide ions to carbonyl and azomethine bonds

Additions of water, hydroxide ions, alcohols and alkoxide ions to carbonyl and azomethine bonds

A simple one pot synthesis of condensed 1,2,4‐triazines by using the tandem a_N‐S_N^ipso and S_N^H‐S_N^ipsa reactions

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

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Recent Advances in the Chemistry of as-Triazinuum Salts

Cited by 29 publications

References 1 publication

Additions of water, hydroxide ions, alcohols and alkoxide ions to carbonyl and azomethine bonds

Additions of water, hydroxide ions, alcohols and alkoxide ions to carbonyl and azomethine bonds

A simple one pot synthesis of condensed 1,2,4‐triazines by using the tandem aN‐SNipso and SNH‐SNipsa reactions

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

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Product

Resources

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A simple one pot synthesis of condensed 1,2,4‐triazines by using the tandem a_N‐S_N^ipso and S_N^H‐S_N^ipsa reactions