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Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1H-Isoindolin-1-Ones.

ABSTRACT: An effective multi-step continuous flow approach towards N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones, including the local anesthetic compound AL-12, has been realized. Compared to the traditional decoupled batch processes, the combined photochemical-thermal-thermal flow setup rapidly provides the desired target compounds in superior yields and significantly shorter reaction times.

SUBMITTER: Mumtaz S

PROVIDER: S-EPMC6943768 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1H-Isoindolin-1-Ones.

Mumtaz Saira S Robertson Mark J MJ Oelgemöller Michael M

Molecules (Basel, Switzerland) 20191211 24

An effective multi-step continuous flow approach towards N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones, including the local anesthetic compound AL-12, has been realized. Compared to the traditional decoupled batch processes, the combined photochemical-thermal-thermal flow setup rapidly provides the desired target compounds in superior yields and significantly shorter reaction times. ...[more]

PMID: 31835663

Similar Datasets

The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones.

Project description:The synthesis of various 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones was realized following a simple three-step process. The protocol utilized the photodecarboxylative addition of readily available carboxylates to N-(bromoalkyl)phthalimides as a versatile and efficient key step. The initially obtained hydroxyphthalimidines were readily converted to the desired N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones via acid-catalyzed dehydration and subsequent nucleophilic substitution with the corresponding secondary amines. The procedure was successfully applied to the synthesis of known local anesthetics (AL-12, AL-12B and AL-5) in their neutral forms.

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Novel 2,3-Dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones: Synthesis and Biological Evaluation.

Project description:Herein we describe the synthesis and evaluation of a series of novel 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones for in vitro cytotoxicity against three human cancer cell lines as well as for potential antimalarial activity against the chloroquine-sensitive strain 3D7 of Plasmodium falciparum. The title compounds were prepared via PdCl₂-mediated endo-dig cyclization of 2-aryl-8-(arylethynyl)-6-bromo-2,3-dihydroquinazolin-4(1H)-ones. The latter were prepared, in turn, via initial Sonogashira cross-coupling of 2-amino-5-bromo-3-iodobenzamide with aryl acetylenes followed by boric acid-mediated cyclocondensation of the intermediate 2-amino-3-(arylethynyl)-5-bromobenzamides with benzaldehyde derivatives. The 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones 4a-k were evaluated for potential in vitro cytotoxicity against the breast (MCF-7), melanoma (B16) and endothelioma (sEnd.2) cell lines. All of the compounds except 4h and 4i were found to be inactive against the three cancer cell lines. Compound 4h substituted with a 4-methoxyphenyl and 4-fluorophenyl groups at the 3- and 5-positions was found to exhibit significant cytotoxicity against the three cancer cell lines. The presence of phenyl and 3-chlorophenyl groups at the 3- and 5-posiitons of the pyrroloquinazolinone 4i, on the other hand, resulted in significant cytotoxicity against vascular tumour endothelial cells (sEnd.2), but reduced activity against the melanoma (B16) and breast cancer (MCF-7) cells except at higher concentrations. The 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones 4a-l were found to be inactive against the chloroquine sensitive 3D7 strain of Plasmodium falciparum.

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Enantioselective synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes.

Project description:The synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes is reported. The β-hydroxyaminoaldehydes were prepared by enantioselective organocatalytic 1,4-addition of N-tert-butyl (tert-butyldimethylsilyl)oxycarbamate to α,β-unsaturated aldehydes (MacMillan protocol). Alkyne addition to the aldehydes followed by alcohol oxidation furnished N-Boc O-TBS-protected β-aminoynones. Removal of the TBS protecting group initiated a 7-endo-dig cyclization to yield previously unknown 3,4-dihydro-1,2-oxazepin-5(2H)-ones. Reductive cleavage of the N-O bond of the oxazepinones and Boc-deprotection provided 2-substituted 2,3-dihydropyridin-4(1H)-ones via 6-endo-trig cyclization. 2,3-Dihydropyridin-4(1H)-ones are versatile intermediates that have been used for the synthesis of many alkaloids. The new protocol allows the synthesis of 3-dihydropyridin-4(1H)-ones carrying an array of substituents at C2 that cannot be prepared from commercial β-amino acids or by one-carbon homologation of proteinogenic amino acids. The use of readily available β-hydroxylaminoaldehydes expands the utility of our previously reported method to prepare 2,3-dihydropyridin-4(1H)-ones from β-amino acids as the source of diversity and chirality. A broad substrate scope is possible because β-aminoaldehydes can be prepared from α,β-unsaturated aldehydes by an enantioselective organocatalytic process.

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2,3-Dihydro-1H-pyrrolizin-1-one.

Project description:There are two nearly identical mol-ecules in the asymmetric unit of the title compound, C(7)H(7)NO. The mol-ecules are nearly planar (r.m.s. deviations of 0.025 and 0.017 Å) and oriented at a dihedral angle of 28.98 (3)°. The two mol-ecules are linked by a C-H⋯O hydrogen bond. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into zigzag chains along the c axis.

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2,2-Dimethyl-2,3-dihydro-1H-perimidine.

Project description:The title compound, C(13)H(14)N(2), was obtained from reaction of diaminona-phthalene with acetone. In both independent mol-ecules in the asymmetric unit, the tricyclic perimidine consists of a planar (r.m.s. deviations = 0.0125 and 0.0181 Å) naphthalene ring system and an envelope conformation C(4)N(2) ringwith the NCN group hinged with respect to the naph-thalene backbone by 36.9 (2) and 41.3 (2)° in the two independent molecules. The methyl substituents are arranged approximately axial and equatorial on the apical C atom. In the crystal, one of the N-H groups of one independent mol-ecule is involved in classical N-H⋯N hydrogen bonding. Short inter-molecular (C/N)-H⋯π(arene) inter-actions, near the short T-shaped limit, link mol-ecules in the absence of strong acceptors.

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1-Benzyl-2,3-dihydro-quinolin-4(1H)-one.

Project description:In the title compound, C(16)H(15)NO, the two aromatic rings are approximately perpendicular; the carbonyl group is twisted out of the adjacent benzene ring by 14.8 (2)°. In the heterocyclic ring, the C atom linked to the carbonyl group and the C atom linked to the N atom have opposite deviations of 0.467 (5) and 0.184 (4) Å, respectively, from the plane of the benzene ring. The N atom lies approximately in the plane of the phenyl ring. There are no conventional hydrogen bonds; the packing of mol-ecules in the crystal structure is stabilized by van der Waals forces.

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2,2,7-Trimethyl-2,3-dihydro-quinazolin-4(1H)-one.

Project description:There are two independent mol-ecules in the the asymmetric unit of the title compound, C(11)H(14)N(2)O. The heterocyclic ring of the bicyclic system has a sofa conformation, with the C atom bearing the two methyl groups displaced by 0.541 (7) Å from the rest of the atoms of the ring [planar to within 0.064 (9) Å]. Mol-ecules are linked into centrosymmetric dimers via N-H⋯O hydrogen bonds.

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1-Methyl-2,3-dihydro-1H-benzimidazole-2-selone.

Project description:The title compound C(8)H(8)N(2)Se, is the product of the reaction of 2-chloro-1-methyl-benzimidazole with sodium hydro-selenide. The mol-ecule is almost planar (r.m.s. deviation = 0.041 Å) owing to the presence of the long chain of conjugated bonds (Se=C-NMe-C=C-C=C-C=C-NH). The C=Se bond length [1.838 (2) Å] corresponds well to those found in the close analogs and indicates its pronounced double-bond character. In the crystal, mol-ecules form helicoidal chains along the b axis by means of N-H⋯Se hydrogen bonds.

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1,3-Bis[(1H-benzotriazol-1-yl)meth-yl]-2,3-dihydro-1H-benzimidazole.

Project description:In the title compound, C(21)H(18)N(8), the two (benzotriazol-1-yl)methyl groups are located in an anti position with respect to the benzimidazoline moiety. The dihedral angles between the benzotriazole ring systems and the central benzimidazoline moiety are 57.03 (4) and 81.01 (3)°. The crystal packing is stabilized by two C-H⋯π inter-actions.

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2,4-Dibromo-2,3-dihydro-1H-inden-1-yl acetate.

Project description:In the title compound, C(11)H(10)Br(2)O(2), the cyclo-pentene ring fused to the benzene ring adopts an envelope conformation, with the C atom attached to the Br atom as the flap. The crystal structure does not exhibit any classical hydrogen bonds. The mol-ecular packing is stabilized by van der Waals forces and ?-? stacking inter-actions with a centroid-centroid distance of 3.811?(4)?Å.

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