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Kalinin, V. N.; Pashchenko, D. N.; Phan Minh She published the article 《Palladium-catalyzed synthesis of 4-heteroaryl and 4-alkynyl-substituted sydnones. 5-Oxido-3-phenyl-1,2,3-oxadiazol-3-ium-4-ylzinc chloride》. Keywords: palladium catalyzed coupling oxidophenyloxadiazoliumylcopper heteroaryl iodide; alkynyl bromide palladium catalyzed coupling oxidophenyloxadiazoliumylcopper; oxidophenyloxadiazoliumylzinc chloride preparation reactivity; sydnone heteroaryl alkynyl.They researched the compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ).Safety of 5-Iodo-2-furaldehyde. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:2689-65-8) here.

A general method is suggested for the synthesis of 4-heteroaryl- and 4-alkynyl-3-Ph sydnones by palladium(0)-catalyzed cross-coupling of 5-oxido-3-phenyl-1,2,3-oxadiazol-3-ium-4-ylcopper (I, R = Cu) with heteroaryl iodides and alkynyl bromides. Thus, I (R = H) was treated sequentially with BuLi, CuBr, and then 2-iodopyridine and Pd(PPh3)4 in THF-C6H6 to give 85% I (R = 2-pyridyl). 5-Oxido-3-phenyl-1,2,3-oxadiazol-3-ium-4-ylzinc chloride (I, R = ZnCl) was synthesized and found to be significantly less reactive than I (R = Cu) and was successfully coupled only with p-iodonitrobenzene and β-bromostyrene.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem