This paper is dedicated to Gordon Gribble on his retirement -indole chemist par excellence and delightful collaborator. A true gentleman and fine chemist.Received 11-08-2017 Accepted 02-12-2018 Published on line 03-14-2018 AbstractA synthesis of 5-(3,3-dimethyl-3H-indol-2-yl)-3-methyl-1H-pyrazolo [3,4-b]pyridines by the reaction of variously substituted aminomethylene malondialdehydes [2-(3,3-dimethyl-3H-indol-2-ylidene)malondialdehydes] with 5-amino-1-aryl-3-methylpyrazoles in the presence of p-toluenesulfonic acid in water is described.

Spiro[pyrido[3,2,pyrimido [4,5-b] Reaction of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (1) with two equivalents of some 6-aminouracils (or 6-amino-2-thiouracil) generates spirocyclic tetrahydrobenzo[if]quinolizines (7). The one-pot, three-component reaction of amido ketone (1) with 6-aminouracil (or 6-amino-2-thiouracil) and a cyclic six-membered 1,3-diketone produces spirocyclic tetrahydropyrrolo[3,2,1-ij]quinolinones (15).

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New pyrazolo[4 0 ,3 0 :5,6]pyrido[2,3-d]pyrimidines, with an associated spiro-3,3 0oxindole attachment, were prepared by three-component combinations of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione with a pair of reactants chosen from a pyrazol-5-one, a pyrazole-5-amine, a barbituric acid, or a 6-aminouracil.