Reactions of triazines and tetrazines with dienophiles (Review)

Prokhorov, Anton M.; Kozhevnikov, Dmitry N.

doi:10.1007/s10593-012-1117-9

Cited by 98 publications

(31 citation statements)

References 128 publications

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“…In this context, thiol‐X and Diels–Alder reactions are metal‐free alternatives that can counter the mentioned disadvantages and can react with different complementary reaction partners. Both reactions have proven their worth and have been explored in great detail in material and polymer science …”

Section: Click and Click‐inspired Reactions For Sequence Buildingmentioning

confidence: 99%

Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers

Martens

Holloway

Prez

2017

Macromol. Rapid Commun.

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During the previous decade, many popular chemical reactions used in the area of "click" chemistry and similarly efficient "click-inspired" reactions have been applied for the design of sequence-defined and, more generally, sequence-controlled structures. This combination of topics has already made quite a significant impact on scientific research to date and has enabled the synthesis of highly functionalized and complex oligomeric and polymeric structures, which offer the prospect of many exciting further developments and applications in the near future. This minireview highlights the fruitful combination of these two topics for the preparation of sequence-controlled oligomeric and macromolecular structures and showcases the vast number of publications in this field within a relatively short span of time. It is divided into three sections according to the click-(inspired) reaction that has been applied: copper-catalyzed azide-alkyne cycloaddition, thiol-X, and related thiolactone-based reactions, and finally Diels-Alder-chemistry-based routes are outlined, respectively.

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Section: Click and Click‐inspired Reactions For Sequence Buildingmentioning

confidence: 99%

Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers

Martens

Holloway

Prez

2017

Macromol. Rapid Commun.

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“…The π-deficient triazines [262] and tetrazines [262,263] are relevant building blocks for more complex molecules as such heterocycles can be used as reactants in LUMO diene-controlled [4+2] inverse electron demand Diels-Alder cycloaddition processes, which efficiently lead to substituted dihydropyridazines, pyridazines, pyrimidines, or pyridine derivatives [264]. The pioneering work dealing with this so-called Carboni-Lindsey reaction has been reviewed by Boger [265].…”

Section: Six-membered Heterocycles With Three or Four Nitrogen: Triazmentioning

confidence: 99%

“…Triazine and tetrazine derivatives are commonly used as commercial dyes [266], as insecticides [267] and more recently as pharmaceutical agents (Figure 17) [268,269]. Many examples of Diels-Alder reactions leading to new series of triazines and tetrazines have been described in the last decade [262], and among them several proceeded through a MW-assisted procedure. In marked contrast to the triazine derivatives, which have been extensively reviewed in recent years, MW-assisted syntheses of tetrazines remain more underreported, and this review has allowed us to highlight some representative preparations of this system.…”

Section: Six-membered Heterocycles With Three or Four Nitrogen: Triazmentioning

confidence: 99%

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

et al. 2016

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This review describes the formation of six-membered heterocyclic compounds and their fused analogues under microwave activation using modern organic transformations including cyclocondensation, cycloaddition, multicomponents and other modular reactions. The review is divided according to the main heterocycle types in order of increasing complexity, starting with heterocyclic systems containing one, two and three heteroatoms and their fused analogues. Recent microwave applications are reviewed, with special focus on the chemistry of bioactive compounds. Selected examples from the 2006 to 2015 literature are discussed.

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“…These cycloadducts have also received increasing interest in the fields of inorganic,3 physical organic4 and medicinal1b,c,5 chemistry. In the recent review,6 the features and peculiarities of the [4+2] cycloaddition reactions of 1,2,4,5‐tetrazines have been comprehensively surveyed, but no base‐catalytic version of this reaction has been mentioned.…”

Section: Synthesis Of 36‐di(pyrrol‐2‐yl)pyridazines 3 From 1245‐tmentioning

confidence: 99%

Superbase‐Catalyzed [4+2] Cycloaddition of Acetylenes to 3,6‐Di(pyrrol‐2‐yl)‐1,2,4,5‐tetrazine: A Facile Synthesis of 3,6‐Di(pyrrol‐2‐yl)pyridazines

et al. 2013

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Acetylenes undergo the [4 + 2] cycloaddition to 3,6-di(pyrrol-2-yl)-1,2,4,5-tetrazine in the potassium hydroxide/dimethyl sulfoxide or potassium tert-butoxide/dimethyl sulfoxide systems (80 8C, 2.5-4 h) to afford (after extrusion of the nitrogen molecule from the intermediate) 3,6-di(pyrrol-2-yl)pyridazines in up to 73% yield, while under non-catalytic conditions this reaction does not take place. This unusual result substantially extends the scope of synthetic application and mechanistic diversity of the Diels-Alder reaction. The step-wise mechanisms involving the formation of [OH/tetrazine] À or [t-BuO/tetrazine] À anionic intermediate complexes or cycloaddition of tetrazine to the acetylide anion are considered.

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Reactions of triazines and tetrazines with dienophiles (Review)

Cited by 98 publications

References 128 publications

Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers

Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

Superbase‐Catalyzed [4+2] Cycloaddition of Acetylenes to 3,6‐Di(pyrrol‐2‐yl)‐1,2,4,5‐tetrazine: A Facile Synthesis of 3,6‐Di(pyrrol‐2‐yl)pyridazines

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