Pyrrolo-pyridines electrophilic substitution

Pyrrolo[2,3-6]pyridine, 2,3-dihydro-electrophilic substitution, 4, 503 nitration, 4, 512 synthesis, 4, 520... 

Only a few investigations of electrophilic substitution reactions of pseudo-azulenes containing a pyrrole-type nitrogen have been reported. There are many examples of alkylations (see Table VI). An alkylation always takes place at the nitrogen of the five-membered ring. For 7H-pyrrolo[2,3-b]-pyridine 68 azocoupling and reaction with dithiolium salts have been reported.166... 

Pyrrolo[3,2-f]pyridine can be readily substituted with a variety of electrophiles at C-2 or C-3 after protection of the ring nitrogen atom. Derivatives can be synthesized with substituents such as iodo, methyl, trimethyltin, formyl, and allyl groups. The reactions proceed with excellent yields (47-95%) <200583581 >. 

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