Abstract
Reaction of 4-bromoacetoacetanilide (II) with pyridine (Ia), 4-methylpyridine (Ib), and 3-methylpyridine (Ic) gave pyridinium (IVa), 4-methylpyridinium (IVb), and 3-methylpyridinium (N-phenylcarbamoyl) acetonylide (IVc), respectively. These ylides (IVa, b, c) were allowed to react with diethyl acetylenedicarboxylate (DEAC) to give diethyl 3-(N-phenylcarbamoyl) acetylpyrrolo [1, 2-a] pyridine-1, 2-dicarboxylate (VIa), and its methyl derivatives (VIb, VIc, and VId). Reaction of ethyl 4-bromoacetoacetate (III) with pyridines (Ia, b, c) followed by treatment with DEAC afforded the pyrrolo [1, 2-a] pyridine derivatives (VIIa, b, c, d). Similarly, quinoline (VIIIa) and 4-methylquinoline (VIIIb) reacted with II (III) to give the corresponding N-ylides, IXa and IXb (Xa and Xb), respectively. These ylides were converted to the pyrrolo [1, 2-a] quinoline derivatives (XIa, b and XIIa, b). Similar reaction of isoquinoline gave the pyrroloisoquinoline derivatives (XIII, XIV).
