A novel approach to fused 1,2,4-triazines by intramolecular cyclization of 1,2-diaza-1,3-butadienes bearing allyl(propargyl)sulfanyl and cyclic tert-amino groups

Belskaia, Natalia P.; Deryabina, T. G.; Koksharov, A. V.; Кодесс, М. И.; Dehaen, Wim; Lebedev, A. T.; Бакулев, В. А.

doi:10.1016/j.tetlet.2007.10.140

Cited by 29 publications

(10 citation statements)

References 12 publications

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“…1 Earlier, 2, 3 we have found that the presence of ter minal S alkyl and 1 azacycloalkyl groups in a diazadiene system radically changes the chemical properties of these compounds. 3 Alkylsulfanyl 2 arylazo 3 (pyrrolidin 1 yl)acrylonitriles react as latent dipoles to give products of intramolecular and intermolecular cyclization.…”

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confidence: 85%

“…1 The structures of pyrrolotriazines 4b-d were confirmed by comparing their physico chemical characteristics with those of authentic samples. 3 Preparation of compounds 2a-f (generat procedure). A solu tion of 3 alkylsulfanyl 2 arylazo 3 (1 azacycloalk 1 yl)acrylo nitrile 1 or 3 (0.5 mmol) and maleimide (0.145 g, 1.5 mmol) in benzene was kept at 50 °C for 7-40 h (TLC).…”

Section: Table 1 Selected Bond Lengths (D) and Bond Angles (ω) In Stmentioning

confidence: 99%

“…13 C NMR, δ: 176.6 (CO); 174.7 (CO); 174.6 (CO); 173.8 (CO); 161.3 (C Ar ); 158.0 (C Ar ); 157.7 (C(4)); 157.1 (C(4)); 146.5 (C Ar ); 146.4 (C Ar ); 136.1 (C Ar ); 125.9 (C Ar ); 125.6 (C Ar ); 123.0 (C Ar ); 122.7 (C Ar ); 115.2 (CN); 114.9 (CN); 105.9 (C(2´)); 104.5 (C(2´)); 72.0 (C(8a)); 71.6 (C(8a)); 60.0 (C(3a)); 59.9 (C(3a)); 50.1 (C(6)); 46.8 (C(6)); 42.3 (C(8b)); 41.9 (C(8b)); 27.9 (C(7)); 27.7 (C(7)); 27. 3 38 (m, 1 H, CH). The mixture of the cis and trans isomers in a ratio of 2 : 3.…”

Section: Table 1 Selected Bond Lengths (D) and Bond Angles (ω) In Stmentioning

confidence: 99%

“…3 With strengthening of the electron donating proper ties of the substituent in the aromatic ring of the starting reagents 3a-d, the content of intramolecular cyclization products 4 in the reaction mixture increases, while the …”

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confidence: 99%

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Reactions of 3-alkylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles with maleimide

Belskaya¹,

Koksharov²,

Deryabina

et al. 2010

Russ Chem Bull

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Reactions of 2 arylazo 3 (1 azacycloalk 1 yl) 3 methylsulfanylacrylonitriles with male imide in benzene gave octahydropyrrolo[3,4 a]pyrrolizines 2a-c, decahydro 2,7a diaza cyclopenta[a]indene 2e, and decahydro 5 oxa 2,7a diazacyclopenta[a]indene 2f as a result of 1,3 dipolar cycloaddition. In a similar reaction with 3 allylsulfanyl 2 arylazo 3 (1 azacycloalk 1 yl)acrylonitriles 3, dipolar cycloaddition and intramolecular cyclization competed to give a mixture of compounds 2 (major products) and 1,4,6,7,8,8a hexahydropyrrolo[2,1 c] 1,2,4 triazines 4b-d, 1,6,7,8,9,9a hexahydro 4H pyrido[2,1 c] 1,2,4 triazine 4e, and 1,4,6,7,9,9a hexahydro 1,4 oxazino[3,4 c] 1,2,4 triazine 4f (minor products).

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mentioning

confidence: 85%

Section: Table 1 Selected Bond Lengths (D) and Bond Angles (ω) In Stmentioning

confidence: 99%

Section: Table 1 Selected Bond Lengths (D) and Bond Angles (ω) In Stmentioning

confidence: 99%

mentioning

confidence: 99%

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Reactions of 3-alkylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles with maleimide

Belskaya¹,

Koksharov²,

Deryabina

et al. 2010

Russ Chem Bull

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“…1,2-Diaza-1,3-butadienes 151, containing allyl(propargyl)sulfanyl and cyclic dialkylamino groups, produced 1,2,4-triazines 152 by thermal cyclization [106,107]. Furthermore, in the case of an allylsulfanyl group it was shown that propene was eliminated in this reaction [106]. in the presence of acids led to dehydrogenation of the heterocycle and hydrogenation of the formed Schiff base resulting in the 1-substituted pyrrole 154 [108].…”

Section: -92%mentioning

confidence: 99%

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

Platonova

Глухарева

Zimovets

et al. 2013

Chem Heterocycl Comp

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The term "tert-amino effect" was proposed in 1972 [1] for the cyclization reactions of tertiary anilines containing various double bonds at the ortho position. Meth-Cohn and Suschitzky [1] referred to the first observation of the tert-amino effect by Pinnow in 1895 [2]. Many different examples of reactions involving the tert-amino effect have now accumulated, and it clearly is a convenient method for the synthesis of an impressive number of nitrogen-containing heterocycles that otherwise might be difficult to obtain. Reviews were published by Reinhoudt in 1990 [3] and by Meth-Cohn in 1996 [4] on heterocyclization reactions that take place by the mechanism of the tert-amino effect. Another review dedicated to 1,6-and 1,8-naphthiridine derivatives was published in 2003 by Quintela [5]. In the review [6] that we published in 2005, attention was focused on the use of such reactions for the synthesis of spiro compounds. In the review [7], published in 2006, the cyclization reactions of ortho-vinylanilines and their heterocyclic aza analogs were considered, and classification according to the method of ring formation was proposed.

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ChemInform Abstract: A Novel Approach to Fused 1,2,4‐Triazines (II) by Intramolecular Cyclization of 1,2‐Diaza‐1,3‐butadienes Bearing Allyl(propargyl)sulfanyl and Cyclic tert‐Amino Groups.

Belskaia¹,

Deryabina²,

Koksharov³

et al. 2008

ChemInform

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A Novel Approach to Fused 1,2,4-Triazines (II) by Intramolecular Cyclization of 1,2-Diaza-1,3-butadienes Bearing Allyl(propargyl)sulfanyl and Cyclic tert-Amino Groups. -(BELSKAIA*, N. P.; DERYABINA, T. G.; KOKSHAROV, A. V.; KODESS, M. I.; DEHAEN, W.; LEBEDEV, A. T.; BAKULEV, V. A.; Tetrahedron Lett. 48 (2007) 52, 9128-9131; Dep. Technol. Org. Synth., Urals State Tech. Univ., Ekaterinburg 620002, Russia; Eng.) -Mischke 15-164

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A novel approach to fused 1,2,4-triazines by intramolecular cyclization of 1,2-diaza-1,3-butadienes bearing allyl(propargyl)sulfanyl and cyclic tert-amino groups

Cited by 29 publications

References 12 publications

Reactions of 3-alkylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles with maleimide

Reactions of 3-alkylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles with maleimide

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

ChemInform Abstract: A Novel Approach to Fused 1,2,4‐Triazines (II) by Intramolecular Cyclization of 1,2‐Diaza‐1,3‐butadienes Bearing Allyl(propargyl)sulfanyl and Cyclic tert‐Amino Groups.

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