Question

.CN CI N. N S CI CN then H20 HN N CI DDQ CI ОН Li S CI CN n-Bu-Li CN CI ОН N. CI I-

Can you please explain ( in words) the mechanism of the above scheme in details.

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Answer #1

In step reaction of thiophene with nBuLi gives Ortho lithiation product. Now Ortho lithiated thiophene is good nucleophile Wich attack on position no 5 of 2 chloro diazine molecule forms negative charge on nitrogen and ring become non aromatic .water molecule gives proton to stabilize negative charge on Nitrogen.Then DDQ oxidation makes ring Aromatic.

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