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Usage

Uses

Used in Pharmaceutical Synthesis:
3,6-DIIODOPYRIDINE-2-CARBONITRILE is used as a key intermediate in the synthesis of various pharmaceuticals due to its ability to form carbon-carbon and carbon-heteroatom bonds. Its unique structural features and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, 3,6-DIIODOPYRIDINE-2-CARBONITRILE serves as a crucial building block for the creation of novel agrochemicals. Its reactivity allows for the synthesis of compounds with enhanced pesticidal properties, contributing to more effective crop protection strategies.
Used in Organic Chemistry Research:
3,6-DIIODOPYRIDINE-2-CARBONITRILE is utilized as a versatile reagent in organic chemistry research. Its potential applications in drug discovery and medicinal chemistry have been extensively studied, making it an important tool for the development of complex organic molecules and the exploration of new chemical reactions.

InChI:InChI=1/C6H2I2N2/c7-4-1-2-6(8)10-5(4)3-9/h1-2H

Upstream product

• 100-70-9 2-Cyanopyridine 

Relevant academic research and scientific papers

Direct metalation of heteroaromatic esters and nitriles using a mixed lithium-cadmium base. Subsequent conversion to dipyridopyrimidinones

(Chemical Equation Presented) All pyridine nitriles and esters were metalated at the position next to the directing group using (TMP) 3CdLi in tetrahydrofuran at room temperature. The 2-, 3-, and 4-cyanopyridines were treated with 0.5 equiv of base for 2 h to afford, after subsequent trapping with iodine, the corresponding 3-iodo, 2-iodo, and 3-iodo derivatives, respectively, in yields ranging from 30 to 61%. Cyanopyrazine was similarly functionalized at the 3 position in 43% yield. Ethyl 3-iodopicolinate and -isonicotinate were synthesized from the corresponding pyridine esters in 58 and 65% yield. Less stable ethyl 4-iodonicotinate also formed under the same conditions and was directly converted to ethyl 4-(pyrazol-1-yl)nicotinate in a two-step 38% yield. All three ethyl iodopyridinecarboxylates were involved in a one-pot palladium-catalyzed cross-coupling reaction/cyclization using 2-aminopyridine to afford new dipyrido[1,2-a:3′,2′-d]pyrimidin-11- one, dipyrido[1,2-a:4′,3′-d]pyrimidin-11-one, and dipyrido[1,2-a:3′,4′-d]pyrimidin-5-one in yields ranging from 50 to 62%. A similar crosscoupling/ cyclization sequence was applied to methyl 2-chloronicotinate using 2-aminopyridine, 2-amino-5-methylpyridine, and 1-aminoisoquinoline to give the corresponding tricyclic or tetracyclic compounds in 43-79% yield. Dipyrido[1,2-a:4′,3′-d]pyrimidin-11-one and dipyrido[1,2-a:3′,4′-d]pyrimidin-5-one showed a good bactericidal activity against Pseudomonas aeroginosa. Dipyrido-[1,2-a:2′,3′-d] pyrimidin-5-one and pyrido[2′,3′:4,5]pyrimidino[2,1-a]isoquinolin-8- one showed a fungicidal activity against Fusarium and dipyrido[1,2-a:4′, 3′-d]pyrimidin-11-one against Candida albicans. Ethyl 4-(pyrazol-1-yl) nicotinate and dipyrido[1,2-a:2′,3′-d]pyrimidin-5-one have promising cytotoxic activities, the former toward a liver carcinoma cell line (HEPG2) and the latter toward a human breast carcinoma cell line (MCF7).

Synthesis of ortho-substituted cyanopyridines through lithio intermediate trapping

Ortholithiation of 4-cyanopyridine using 2,2,6,6-tetramethylpiperidide (LiTMP) and trapping the lithio intermediate with electrophiles represents an efficient and straightforward access to ortho-substituted-4-cyanopyridines. The cyano group can be used as an ortho-directing group and allows the preparation of 3-halogeno-4-cyanopyridines. Reactivity of 2- and 3-cyanopyridines is also investigated and seems to give similar results.