Simple exploration of 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline

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Studies with enamines and azaenamines: Synthesis and reactivity of 3-dimethylamino-2-[(3-indolyl) carbonyl]propenonitrile

(Chemical Equation Presented) 2-Oxo-3-(indol-3-yl)propanonitrile 2 condensed with dimethylformamide dimethylacetal to yield the enaminonitrile 3. The latter reacted with 4-chloroaniline to yield the 4- chlorophenylaminoacrylonitrile 5. Reaction of 3 with hydrazine hydrate led to formation of pyrazole-4-carbonitrile 6. Compound 3 reacted with ethyl acetoacetate in refluxing acetic acid and in presence of ammonium acetate to yield the indolylpyridine 10. Enamine 3 reacted with 5(1H)-aminotriazole 13 and 3(5)-aminopyrazole 17 to yield the pyrimidine derivatives 15 and 19, respectively.

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Reference：
Isoquinoline – Wikipedia,
Isoquinoline | C9H2601N – PubChem