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Kruglenko, V. P.; Gnidets, V. P.; Klyuev, N. A.; Povstyanoi, M. V.

doi:10.1023/a:1019573532428

Cited by 11 publications

(6 citation statements)

References 1 publication

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“…Similarly, treatment of 5 with malonic or β-ethoxymethylenemalonic acid derivatives gave pyrimido[1,2-a]benzimidazole derivatives, again from a 1,3-NCN reaction [7]. However, reactions of diamine 5 as a 1,4-NCNN bis-nucleophile with β-dicarbonyl compounds, under acid catalysis, to provide 1,2,4-triazepino[2,3-a]benzimidazoles, were also reported [8].…”

Section: Resultsmentioning

confidence: 97%

5-Amino-3-(diethylamino)-5H-benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine 1,1-Dioxide

Tran

Forsyth

Francis

2018

Molbank

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In the quest for discovery of novel bioactive molecules, new heterocyclic ring systems provide templates for exploration of uncharted chemical space. Herein, we describe the synthesis of a new benzo [4,5] ,2,4,6]thiatriazine derivative from readily available 1,2-diaminobenzimidazole and N,N-diethyl-N -chlorosulfonyl chloroformamidine. The product structure, confirmed by X-ray crystallography, bears an exocyclic NH 2 group, which should enable synthesis of an extended range of derivatives of this unusual scaffold.Abstract: In the quest for discovery of novel bioactive molecules, new heterocyclic ring systems provide templates for exploration of uncharted chemical space. Herein, we describe the synthesis of a new benzo [4,5]imidazo[1,2-b][1,2,4,6]thiatriazine derivative from readily available 1,2-diaminobenzimidazole and N,N-diethyl-N′-chlorosulfonyl chloroformamidine. The product structure, confirmed by X-ray crystallography, bears an exocyclic NH2 group, which should enable synthesis of an extended range of derivatives of this unusual scaffold.

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Section: Resultsmentioning

confidence: 97%

5-Amino-3-(diethylamino)-5H-benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine 1,1-Dioxide

Tran

Forsyth

Francis

2018

Molbank

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“…for the synthesis of 1,2,4‐triazepano[2,3‐ a ]benzimidazoles 101 via the condensation reaction of diaminobenzimidazole 100 with a diketone such as pentane‐2,4‐dione, 4‐phenylbutane‐2,4‐dione, and dibenzoylmethane in PPA at 110–115°C. In another attempt, Kruglenko and coworkers synthesized a large series of 2‐substituted 5 H ‐1,2,4‐triazepano[2,3‐ a ]benzimidazol‐4‐one derivatives 102 in good yield through the condensation of different diketones such as the acetoacetic ester and 1,3‐diethoxycarbonylacetone with diaminobenzimidazole 100 in boiling AcOH (Scheme ) …”

Section: Discussionmentioning

confidence: 99%

Overview on Developed Synthesis Methods of Triazepane Heterocycles

Zeydi

2017

J Chinese Chemical Soc

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Triazepanes are important seven‐membered heterocyclic compounds with nitrogen at different positions in the ring, and have many pharmaceutical activities. Compounds with the triazepane core have attracted much attention as a result of their interesting biological properties. A study of the literature shows that there are various methods for the preparation of triazepanes. In this review, we have classified the methods based on the nitrogen position in the final triazepine products into four triazepine classes, namely TAP‐1,2,3, TAP‐1,2,4, TAP‐1,2,5, and TAP‐1,3,5.

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“…Oxidation of imidazo [1,2-b]pyridazine (112) to an N-oxide has been reported (Scheme 28). [135] The reaction is carried out using 85% hydrogen peroxide in polyphosphoric acid and took place selectively at the six-membered ring to yield the 5-oxide 171.…”

Section: Methods 4: Oxidation Of the Ring Nitrogen Atommentioning

confidence: 99%

“…[72,73] Protonation of some substituted derivatives has been studied in detail spectrophotometrically as well as by means of NMR spectroscopy. Thus, imidazo[1,2-b]pyridazine (112) undergoes deuterium exchange at 95 8C in deuterosulfuric acid with a half-life of 24 hours at position 3 (e.g., 120; Scheme 20); in turn, this exchange is complete in 1.5 minutes in sodium deuteroxide and takes place at position 8 selectively (when 121 is formed). 1-alkyl derivatives are formed, mostly in good yield.…”

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confidence: 99%

Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

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In contrast to Section 12.5.1.1.1.1, where in most cases the first reaction step is the quaternization of a pyridin-2-amine derivative followed by nucleophilic attack of the 2-amino group on an appropriate functional group to form the imidazole ring, several ring closures have been elaborated starting from substituted pyridin-2-amines. In these cases, the â-carbon atom of the carbon chain attached to the 2-amino group bears an appropriate functional group, and a nucleophilic attack of the pyridine ring nitrogen atom at this center results in formation of the imidazole ring. Such syntheses are shown in Scheme 8.

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Cited by 11 publications

References 1 publication

5-Amino-3-(diethylamino)-5H-benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine 1,1-Dioxide

5-Amino-3-(diethylamino)-5H-benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine 1,1-Dioxide

Overview on Developed Synthesis Methods of Triazepane Heterocycles

Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

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