Bulletin of the Chemical Society of Japan p. 2543 - 2548 (1999)
Update date:2022-07-30
Topics:
Ito, Shunji
Morita, Noboru
Asao, Toyonobu
The reaction of 1-azulenecarbaldehydes 9a and b with pyrrole (8) in acetic acid resulted in decarbonylation to afford azulenes even at room temperature in 49 and 78% yields, respectively. 1,3-Azulenedicarbaldehydes also reacted with 8 to give azulenes in 36 and 52% yields, respectively. This decarbonylation reaction was adopted to the selective synthesis of 3,3'- unsubstituted di(1-azulenyl)methane derivatives 7a-d. Acid-catalyzed condensation of 9a and b with paraformaldehyde or benzaldehyde afforded 3,3'- methylenedi(1-azulenecarbaldehyde)s, following this decarbonylation reaction gave the desired 7a-d as a sole product in 33-59% yields starting from 9a and b. Such decarbonylation is because of the ability of protonation of azulene ring in acidic condition and because of electron-donating properties of pyrrole ring. This reaction would serve as a new strategy for the protection of 1- and/or 3-positions of azulene ring.
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