ChemInform Abstract: CONDENSED AS‐TRIAZINES. VII. A SIMPLIFIED METHOD FOR THE SYNTHESIS OF BENZO‐AS‐TRIAZINE DERIVATIVES

Messmer, A.; Hajós, Gy.; Benko, P.; Pallos, L.

doi:10.1002/chin.198022247

Cited by 4 publications

(7 citation statements)

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“…Cyclisation of N-(2-nitrophenyl)-N 0 -benzoylthiourea and its derivatives (compounds 25) in an alkaline medium affords the corresponding 1,2,4-benzotriazine-3(2H)-thione 1-oxides 26. 30 The reaction of o-nitroaniline and its 4-substituted derivatives (compounds 27) with cyanamide gives 3-amino-1,2,4-benzotriazine 1-oxides 28. 22 3.…”

Section: Methods For the Synthesis Of 124-triazine N-oxidesmentioning

confidence: 99%

1,2,4-TriazineN-oxides and their annelated derivatives

Kozhevnikov¹,

Русинов²,

Чупахин³

1998

Russ. Chem. Rev.

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This review deals with the synthesis and properties of 1,2,4-triazine N-oxides and their annelated derivatives. Methods for the incorporation of the N-oxide group in the 1,2,4-triazine ring by direct oxidation and cyclisation involving nitro, nitroso, and isonitroso groups are discussed. Reactions of 1,2,4-triazine N-oxides with electrophiles, nucleophiles, and dienophiles are considered. The effect of the N-oxide group on the chemical shifts in the 1 H, 13 C, and 14 N NMR spectra and the specific features of decomposition of 1,2,4-triazine N-oxides under electron impact are analysed. The bibliography includes 107 references.

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Section: Methods For the Synthesis Of 124-triazine N-oxidesmentioning

confidence: 99%

1,2,4-TriazineN-oxides and their annelated derivatives

Kozhevnikov¹,

Русинов²,

Чупахин³

1998

Russ. Chem. Rev.

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“…45 It should be mentioned that 3-chlorophenanthro[9,10-e][1,2,4]triazine, a ring-condensed analogue of the benzo [e] [1,2,4]triazine, was demonstrated to react with trialkyl phosphites to give phosphonate esters in good yields. 47 In another approach, nucleophilic substitution of the C(3)−SMe group 48 with secondary amines, 48 hydrazine, 28 and MeO 49 was described. Surprisingly, neither chloride 1c nor any other C(3) halides have been investigated in Pd-catalyzed C−C cross-coupling reactions, even though such a process could, in principle, provide an easy access to a variety of (het)aryl, alkyl, and other substituents at the C(3) position of the benzo [e] [1,2,4]triazine ring.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Comparison of Methods for Preparation of Functional Derivatives 1 in This Work and Previously Used a See Figure 2 for methods. b Refs 35, 61. c Ref 36. d Ref 33. e Refs 24,48. , the mixture was filtered through Celite and the solvent was evaporated giving 0.892 g (99% yield; 95−99% in several runs) of amine 1b as a yellow solid.Method B.…”

mentioning

confidence: 99%

3-Substituted Benzo[e][1,2,4]triazines: Synthesis and Electronic Effects of the C(3) Substituent

et al. 2019

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A series of 19 structurally diverse C(3)substituted derivatives of benzo [e][1,2,4]triazine were synthesized from 3-chloro-(1c) and 3-iodobenzo[e][1,2,4]triazine (1d) obtained in three steps from 2-nitroaniline in 37−55% yields. Nucleophilic aromatic substitution and metal-catalyzed (Pd, Cu) reactions led to functional derivatives that include alkyl (C 5 H 11 ), (het)aryl (Ph, 2-thienyl, ferrocenyl), ArCC, amine (NHPh and morpholine), PO(OEt) 2 , sulfanyl (SBu-t), alkoxide (OEt, OMe), and CN. The synthesis of C(3)−CF 3 derivative 1g via the Ruppert reaction with 1d and its 1-oxide analogue 2d led to the substitution followed by formal addition of HCF 3 to the CN bond. Pd-catalyzed carbonylation reactions of 1d and 2d did not give the corresponding C(3)-carboxylic acids. Therefore, acid 1f was obtained through hydrolysis of the CN. The substituent effect on the electronic structure of the benzo[e][1,2,4]triazine ring was investigated by spectroscopic methods (UV−vis and NMR) augmented with density functional theory calculations. Results show significant effect of the C(3) substituent on the π−π*(1) transition energy and good correlation of the 1 H NMR chemical shift with the substituent constant σ p . Molecular and crystal structures of six derivatives were established with the single-crystal X-ray diffraction method, and the substituent impact on the molecular geometry was investigated.

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“…As a continuation of these studies the question arose as to whether unsaturated six-membered heterocycles could be similarly transformed and owing to the results of some earlier intensive investigations on triazines [17][18][19] we decided to investigate the possible transformations of this ring system. Although partially reduced 1,2,4-triazines and their benzologs (i.e.…”

Section: Resultsmentioning

confidence: 99%

Selective Synthesis and Cycloaddition Reactions of New Azomethine Imines Containing a 1,2,4‐Triazine Ring

et al. 2005

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ChemInform Abstract: CONDENSED AS‐TRIAZINES. VII. A SIMPLIFIED METHOD FOR THE SYNTHESIS OF BENZO‐AS‐TRIAZINE DERIVATIVES

Abstract: Ausgehend von ortho‐Nitroanilinen (I) werden in einer zweistufigen Synthese die asymmetrischen Mercapto‐triazin‐N‐oxide (IV) hergestellt.

Cited by 4 publications

References 0 publications

1,2,4-TriazineN-oxides and their annelated derivatives

1,2,4-TriazineN-oxides and their annelated derivatives

3-Substituted Benzo[e][1,2,4]triazines: Synthesis and Electronic Effects of the C(3) Substituent

Selective Synthesis and Cycloaddition Reactions of New Azomethine Imines Containing a 1,2,4‐Triazine Ring

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