97780-97-7

Usage

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 461, 1985 DOI: 10.1016/S0040-4039(00)61911-1

InChI:InChI=1/C11H11N/c1-9(2)7-10-3-5-11(8-12)6-4-10/h3-6H,1,7H2,2H3

Upstream product

• 623-26-7 terephthalonitrile 
• 18292-38-1 2-methallyltrimethylsilane 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 3058-39-7 4-iodobenzonitrile 
• 126747-14-6 4-cyanophenylboronic acid 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 115-11-7 isobutene 

Relevant academic research and scientific papers

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Original antileishmanial hits: Variations around amidoximes

In continuation to our previous findings on amidoximes' antiparasitic activities, a new series of 23 original derivatives was designed and obtained by convergent synthesis. First, new terminal alkenes were synthesized by cross-coupling reaction. Then, cyclization was performed between terminal alkenes and β-ketosulfones using manganese(III) acetate reactivity. Twenty-three amidoximes were tested for their in vitro activity against Leishmania amazonensis promastigotes and their toxicity on murine macrophages. Seven of the tested compounds exhibited an antileishmanial activity at lower than 10 μM with moderate to low toxicity. Six of these molecules showed activity at lower than 10 μM against promastigotes and toxicity at higher than 50 μM were selected and evaluated for their activity against intracellular Leishmania amazonensis amastigotes. Modulating chemical substituents in position 2 of dihydrofuran highly influenced their antileishmanial activities. The introduction of a methyl or trifluoromethyl group on the benzene ring of the benzyl group had a positive influence on activity without significantly increasing toxicity (52, 59, 60).

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Dehydroformylation, or the reaction of aldehydes to produce alkenes, hydrogen gas, and carbon monoxide, is a powerful transformation that is underdeveloped despite the high industrial importance of the reverse reaction, hydroformylation. Interestingly, nature routinely performs a related transformation, oxidative dehydroformylation, in the biosynthesis of cholesterol and related sterols under mild conditions using base-metal catalysts. In contrast, chemists have recently developed a non-oxidative dehydroformylation method; however, it requires high temperatures and a precious-metal catalyst. Careful study of both approaches has informed our efforts to design a base-metal catalyzed, mild dehydroformylation method that incorporates benefits from each while avoiding several of their respective disadvantages. Importantly, we show that cooperative base metal catalysis presents a powerful, mechanistically unique approach to reactions which are difficult to achieve using conventional catalyst design.

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Direct one-pot syntheses of 4-(ω-alkenyl)-benzonitriles in high yields have been achieved via the reaction of terephthalonitrile dianion with allyl or co-alkenyl bromides in liquid ammonia. Georg Thieme Verlag Stuttgart.

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