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Transformation of 3-(Furan-2-yl)-1,3-di(het)arylpropan-1-ones to Prop-2-en-1-ones via Oxidative Furan Dearomatization/2-Ene-1,4,7-triones Cyclization.

ABSTRACT: The approach to 3-(furan-2-yl)-1,3-di(het)arylprop-2-en-1-ones based on the oxidative dearomatization of 3-(furan-2-yl)-1,3-di(het)arylpropan-1-ones followed by an unusual cyclization of the formed di(het)aryl-substituted 2-ene-1,4,7-triones has been developed. The cyclization step is related to the Paal-Knorr synthesis, but the furan ring formation is accompanied in this case by a formal shift of the double bond through the formation of a fully conjugated 4,7-hydroxy-2,4,6-trien-1-one system or its surrogate.

SUBMITTER: Shcherbakov RO

PROVIDER: S-EPMC8124928 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(E)-2-(2-Nitro-prop-1-en-yl)furan.

Project description:Crystals of the title compound, C(7)H(7)NO(3), under Mo K? radiation sublime in less than 1h at room temperature. However, it was possible to collect data at 100K. It crystallized as the E isomer only. A double-bond conjugation in the furan ring is extended to the nitro-alkenyl group. Mol-ecular associations were realized in the crystal through N?? [3.545?(2)?Å] inter-actions involving the furan ring and C-H?O hydrogen bonds.

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Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Project description:Enantioenriched, polycyclic compounds were obtained from a simple acylphloroglucinol scaffold. Highly enantioselective dearomatization was accomplished using a Trost ligand-palladium(0) complex. A computational DFT model was developed to rationalize observed enantioselectivities and revealed a key reactant-ligand hydrogen bonding interaction. Dearomatized products were used in visible light-mediated photocycloadditions and oxidative free radical cyclizations to obtain novel polycyclic chemotypes including tricyclo[4.3.1.01,4]decan-10-ones, bicyclo[3.2.1]octan-8-ones and highly-substituted cycloheptanones.

| S-EPMC5222469 | biostudies-literature

(E)-3-(Furan-2-yl)-1-(4-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C(14)H(12)O(3), the prop-2-en-1-one unit forms dihedral angles of 12.96 (5) and 7.89 (7)° with the 4-meth-oxy-phenyl group and the furan ring, respectively. The furan and benzene rings form a dihedral angle of 8.56 (5)°. In the crystal, C-H⋯π and π-π inter-actions are observed between the benzene and heterocyclic rings [centroid-centroid distance = 3.760 (1) Å].

| S-EPMC3238853 | biostudies-literature

(E)-3-(Anthracen-9-yl)-1-(furan-2-yl)prop-2-en-1-one.

Project description:In the mol-ecule of the title heteroaryl chalcone derivative, C(21)H(14)O(2), the almost planar prop-2-en-1-one unit [r.m.s. deviation = 0.0087?(1)?Å] forms dihedral angles of 5.81?(7) and 49.85?(6)°, respectively, with the furan ring and anthracene ring system. In the crystal structure, the mol-ecules are linked into a two-dimensional network parallel to (100) by C-H?O hydrogen bonds and ??? inter-actions involving the furan rings [centroid-centroid distance = 3.7205?(6)?Å].

| S-EPMC2983903 | biostudies-other

The crystal structures of six (2E)-3-aryl-1-(5-halogeno-thio-phen-2-yl)prop-2-en-1-ones.

Project description:The structures of six chalcones containing 5-halogeno-thio-phen-2-yl substituents are reported: (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13ClOS, (I), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13BrOS, (II), are isostructural in space group P-1, while (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one, C15H13ClO2S, (III), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one C15H13BrO2S, (IV), are isostructural in space group P21/c. There are no hydrogen bonds of any kind in the structures of compounds (I) and (II), but in the structures of compounds (III) and (IV), the mol-ecules are linked into C(7) chains by means of C-H?O hydrogen bonds. In the structure of (2E)-3-(4-bromo-phen-yl)-1-(5-chloro-thio-phen-2-yl)prop-2-en-1-one, C13H8BrClOS, (V), there are again no hydrogen bonds nor ?-? stacking inter-actions but in that of (2E)-1-(5-bromo-thio-phen-2-yl)-3-(3-meth-oxy-phen-yl)prop-2-en-1-one, C14H11BrO2S, (VI), the mol-ecules are linked into C(5) chains by C-H?O hydrogen bonds. In each of compounds (I)-(VI), the mol-ecular skeletons are close to planarity, and there are short halogen?halogen contacts in the structures of compounds (II) and (V) and a short Br?O contact in the structure of compound (VI). Comparisons are made with the structures of some similar compounds.

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(E)-1-(Furan-2-yl)-3-(2,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title chalcone derivative, C(16)H(16)O(5), the dihedral angle between the furan and benzene rings is 2.06?(17)°. The two meth-oxy groups at the ortho and para positions are essentially coplanar with the benzene ring [C-O-C-C angles = -1.0?(5) and 178.5?(3)°], whereas the third one at the meta position is slightly twisted [C-O-C-C = 9.6?(5)°]. In the crystal, weak C-H?O inter-actions link the mol-ecules into a sheet parallel to ([Formula: see text]02). An inter-molecular ?-? inter-action between the furan and benzene rings is present [centroid-centroid distance = 3.772?(2)?Å]. A short C?C contact [3.173?(5)?Å] is also observed between neighbouring furan rings.

| S-EPMC3275007 | biostudies-other

2,2-[(E)-3,3-Diphenyl-prop-2-ene-1,1-di-yl]bis-(3-hy-droxy-cyclo-hex-2-en-1-one).

Project description:In the title compound, C(27)H(26)O(4), each of the cyclo-hexenone rings adopts a half-chair conformation. The dihedral angle between the two phenyl rings is 89.53?(5)°. The hy-droxy and carbonyl O atoms face each other and are orientated to allow the formation of two intra-molecular O-H?O hydrogen bonds, which are typical of xanthene derivatives.

| S-EPMC3239045 | biostudies-literature

Crystal structure of (2E)-1-(1-benzo-furan-2-yl)-3-(2-bromo-phen-yl)prop-2-en-1-one monohydrate.

Project description:The title compound, C17H11BrO2·H2O, crystallizes as a monohydrate in the chiral ortho-rhom-bic space group P212121, and has non-linear optical (NLO) properties. The mol-ecule has an E conformation about the C=C bond and is relatively planar with the benzo-furan and bromo-phenyl rings being inclined to one another by 10.60?(14)°. In the crystal, the water mol-ecule is linked to the organic mol-ecule by O-H?O hydrogen bonds, forming an R (2) 2(7) ring motif while C-H?O hydrogen bonds lead to the formation of helices along the b-axis direction.

| S-EPMC4645062 | biostudies-literature

Three closely related (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(meth-oxy-phen-yl)prop-2-en-1-ones]: supra-molecular assemblies in one dimension mediated by hydrogen bonding and C-H?? inter-actions.

Project description:In the title compounds, (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(2-meth-oxy-phen-yl)prop-2-en-1-one], C26H22O4 (I), (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(3-meth-oxy-phen-yl)prop-2-en-1-one], C26H22O4 (II) and (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one], C28H26O6 (III), the asymmetric unit consists of a half-mol-ecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98?(8), 7.74?(7) and 7.73?(7)° for (I), (II) and (III), respectively. In the crystal of (I), mol-ecules are linked by pairs of C-H?? inter-actions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C-H?O hydrogen bonds, forming R22(16) and R22(14) ring motifs, respectively, as parts of [201] and [101] chains, respectively.

| S-EPMC5458319 | biostudies-literature

N'-(Furan-2-ylmethyl-ene)-2-hydroxy-benzohydrazide.

Project description:In the title mol-ecule, C(12)H(10)N(2)O(3), the aromatic and furan rings form a dihedral angle of 8.89?(1)° and an intra-molecular N-H?O hydrogen bond occurs. In the crystal structure, inter-molecular O-H?O hydrogen bonds link the mol-ecules into zigzag chains running along the c axis.

| S-EPMC2959693 | biostudies-literature

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