Sequential Three-Component and Heck Reactions for the Synthesis of Phenanthridones

Abstract

A condensation-cycloaddition-cross-coupling reaction sequence has been applied to the synthesis of phenanthridone derivatives. This novel two-step procedure is based on a three-component reaction to give 2-halobenzamide-substituted cyclohexenes, which undergo palladium-catalyzed intramolecular Heck cyclizations.

domino reactions - Heck reactions - isomerizations - heterocycles - palladium

References

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<A NAME="RZ02705SS-13">13</A>

See also Supporting Information of ref. 5a.

<A NAME="RZ02705SS-14">14</A>

Suitable crystals of 10a were obtained by recrystallization from toluene-EtOAc (10:1).

<A NAME="RZ02705SS-15">15</A>

X-ray data of 10a were collected with a STOE-IPDS diffractometer using graphite-monochromated Mo-K _α radiation (λ = 0.71069 Å). The structure was solved by direct methods [16a] and refined by full matrix least square techniques against F ^² . [16b] XP (Bruker AXS) was used for structure representation. All non-hydrogen atoms were refined anisotropically. The hydrogen atoms (except NH) were included at calculated positions and refined by the riding model. Crystal data for 10a: space group Pna2₁, orthorhombic, a = 13.328 (3), b = 9.314 (2), c = 18.207 (4) Å, V = 2260.2 (9) ų, Z = 8, ρ_calcd = 1.318 g cm^-3, 11205 reflections measured, 3580 were independent of symmetry and 2524 were observed [I > 2σ (I)], R1 = 0.043, wR2 (all data) = 0.091, 315 parameters.

<A NAME="RZ02705SS-16A">16a</A> SHELXS-86: Sheldrick GM. Acta Crystallogr., Sect. A  1990,  46:  467 

<A NAME="RZ02705SS-16B">16b</A> Sheldrick GM. SHELXL-93   University of Göttingen; Germany: 1993.