Cyclopentanone reacts with arylidenemalononitriles 1a–c to give dihydro‐4,6‐indenedicarbonitriles 5a–c. Similarly, the diethyl dihydro‐4,6‐indenedicarboxylate derivative 6 is formed when treating ethyl α‐cyanocinnamate (1d) with cyclopentanone. Cyclopenta[b]pyrans 5a–c are obtained from the reaction of diarylidene derivatives of cyclopentanone with malononitrile.
Benzo[b]pyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, pyrano[3,2-h]quinolines, and pyrano[3,2-c]quinolines were synthesized by the reaction of cinnamonitriles with phenols, naphthols, 8-hydroxyquinoline, and 1-methyl-4-hydroxy-2-quinoline.
Naphtho[2,1-b:5,6-b']dipyrans and naphtho[1,2-b:6,5-b']dipyrans were synthesized by the reaction of cinnamonitriles with 2,3-, 1,5-, 1,6-naphthalenediols, respectively. Polysubstituted pyridines, 2H-pyrans and 4H-pyrans were also synthesized from cinnamonitriles, 2-hydroxyacetophenone and 3-acetyl-4-hydroxy-1-methylcarbostyril, respectively.
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