Preparation of new nitrogen-bridged heterocycles. 42. Synthesis and the reaction of pyridinium N-ylides using bifunctional ethyl thiocyanatoacetates was written by Kakehi, Akikazu;Ito, Suketaka;Hashimoto, Yasunobu. And the article was included in Bulletin of the Chemical Society of Japan in 1996.Formula: C7H7ClN2 This article mentions the following:
Various pyridinium (monosubstituted methylide)s I (R2, R3, R4 = H, Me; R5 = cyano, CO2Et, COMe, COPh) were smoothly attached to the cyano group in Et thiocyanatoacetate or Et 2-thiocyanatopropionate to afford the corresponding pyridinium (substituted cyanomethylide)s II in low-to-moderate yields, while pyridinium (unsubstituted amidate)s III (R1, R2, R3 = H, Me) reacted with the ester carbonyl group in the same reagents to give pyridinium (thiocyanatoacetato)- or (2-thiocyanatopropiono)amidates IV in considerable yields. The 1,3-dipolar cycloadditions of some pyridinium (unsym. substituted cyanomethylide)s with di-Me acetylenedicarboxylate (DMAD) in various solvents afforded only di-Me 3-cyanoindolizine-1,2-dicarboxylate, except for a few examples. On the other hand, the treatment of pyridinium (thiocyanatoaceto)- or (2-thiocyanatopropiono)amidates with a strong base, such as potassium tert-butoxide, gave new bicyclic mesoionic compounds, N-[2-(1,3,4-thiadiazolo[3,2-a]pyridinio)]acetamidate derivatives V, in moderate yields. The intermediacy of N-[1-(2-thiocyanatopyridinio)]acetamidates in the formation reactions of the latter compounds was also proven by independent syntheses. In the experiment, the researchers used many compounds, for example, 1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3Formula: C7H7ClN2).
1-(Cyanomethyl)pyridin-1-ium chloride (cas: 17281-59-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 锜?bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the 锜?bonds. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Formula: C7H7ClN2