Sequential Knoevenagel Condensation/Cyclization for the Synthesis of Indene and Benzofulvene Derivatives.

ABSTRACT: Sequential Knoevenagel condensation/cyclization leading to indene and benzofulvene derivatives has been developed. The reaction of 2-(1-phenylvinyl)benzaldehyde with malonates gave benzylidene malonates, cyclized indenes, and dehydrogenated benzofulvenes. The product selectivity depends on the reaction conditions. The reaction with piperidine, AcOH in benzene at 80 °C for 1.5 h gave a benzylidene malonate in 75% yield as a major product. The reactions with piperidine, AcOH in benzene at 80 °C for 17 h and with TiCl₄-pyridine at room temperature gave an indene derivative in 56 and 79% yields, respectively, as a major product. The reaction with TiCl₄-Et₃N gave a benzofulvene in 40% yield selectively. Indene was transformed to a benzofulvene derivative using t

SUBMITTER: Yamazaki S 

PROVIDER: S-EPMC8552470 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature