Work

(7aR,7bR)-7a,7b-Dihydro-15H-dibenzo[f,f′]cyclopenta[1,2-b:5,4-b′]dichromene

Year: 2025

Type: article

Abstract: The reaction of a 2-naphthol-derived Mannich base with the push-pull 5-morpholinopenta-2,4-dienal under acidic conditions unexpectedly afforded (7aR*,7bR*)-7a,7b-dihydro-15H-dibenzo[f,f′]cyclopenta[1,2-b:5,4-b′]dichromene. The structure of this product was unambiguously confirmed by NMR spectroscopy and X-ray diffraction analysis. A plausible mechanism involves the in situ generation of 1,2-naphthoquinone-1-methide, followed by a [4 + 2] cycloaddition and a subsequent interrupted iso-Nazarov cyclization. In this process, the enol tautomer of the resulting fused cyclopentenone is trapped by a second equivalent of the 1,2-naphthoquinone-1-methide, leading to the observed polycyclic framework.

Source: Molbank

DOI: 10.3390/m2096

Authors: Dmitry V. Osipov, Oleg P. Demidov, Vitaly A. Osyanin

Institutions: Samara State Technical University, North-Caucasus Federal University, Togliatti State University

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $603

Funder: Russian Science Foundation