benzofurans and indoline

We report the access to the benzofuro[3,2-b]indoline framework of phalarine from benzofuran-2-ones via the Fischer indolization reaction which was interrupted at the deamination step. Unexpectedly, allyl nucleophiles did not add to the aminal position of these benzofuro[3,2-b]indoline amines but to the adjacent ring junction center in the presence of trifluoroborane to deliver 3,3-disubstituted indolines containing a difluoroboron-containing six-membered ring with fluorescence properties.

Topics: Alkaloids; Amines; Benzofurans; Boron Compounds; Deamination; Fluorescent Dyes; Halogenation; Indoles

The generation of indolines and benzofurans from the combination of Suzuki-Miyaura coupling reactions with oxidative cyclizations is described.

Topics: Benzofurans; Catalysis; Cyclization; Indoles; Molecular Structure; Oxidation-Reduction

Catalyzed by DBU or DBN, 2-acetoxy benzofuranones and 2-acetoxy-N-Tos indolin-3-ones, were readily prepared from o-acyl phenols and o-acyl anilines, respectively, reacted with H(2)O or a range of amines to afford o-OH and o-NH-Tos benzoic acids or benzoamides in moderate to excellent yields.

Topics: Amides; Benzofurans; Benzoic Acid; Carbon; Catalysis; Indoles; Ketones

The stereospecific oxidation of indan and indene was examined with mutant and recombinant strains expressing naphthalene dioxygenase of Pseudomonas sp. strain 9816-4. Pseudomonas sp. strain 9816/11 and Escherichia coli JM109(DE3)[pDTG141] oxidized indan to (+)-(1S)-indanol, (+)-cis-(1R,2S)-indandiol, (+)-(1S)-indenol, and 1-indanone. The same strains oxidized indene to (+)-cis-(1R,2S)-indandiol and (+)-(1S)-indenol. Purified naphthalene dioxygenase oxidized indan to the same four products formed by strains 9816/11 and JM109(DE3)[pDTG141]. In addition, indene was identified as an intermediate in indan oxidation. The major products formed from indene by purified naphthalene dioxygenase were (+)-(1S)-indenol and (+)-(1R,2S)-indandiol. The results show that naphthalene dioxygenase catalyzes the enantiospecific monooxygenation of indan to (+)-(1S)-indanol and the desaturation of indan to indene, which then serves as a substrate for the formation of (+)-(1R,2S)-indandiol and (+)-(1S)-indenol. The relationship of the desaturase, monooxygenase, and dioxygenase activities of naphthalene dioxygenase is discussed with reference to reactions catalyzed by toluene dioxygenase, plant desaturases, cytochrome P-450, methane monooxygenase, and other bacterial monooxygenases.

Topics: Benzofurans; Biodegradation, Environmental; Dioxygenases; Electron Transport; Hydroxylation; Indans; Indenes; Indoles; Multienzyme Complexes; Oxygenases; Pseudomonas; Recombinant Proteins; Stereoisomerism; Substrate Specificity