Synthesis of fused azolones from ortho-substituted arenecarbohydroxamic acids

Hershenson, Fred M.; Bauer, Ludwig; King, Kenneth F.

doi:10.1021/jo01270a093

Cited by 25 publications

(10 citation statements)

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“…2-Benzimidazolone (1-H 2 ) . From 5.0135 g of 1,2-phenylenediamine: 2.0181 g, 47%; 1 H NMR (400 MHz, DMSO- d 6 ) δ 10.60 (br s, 2H), 6.91 (s, 4H (two overlapping signals)); 13 C NMR (100 MHz, DMSO- d 6 ) δ 160.57, 134.88, 125.70, 113.78; HRMS (M) calcd for C 7 H 6 N 2 O 134.0480, found 134.0482.…”

Section: Methodsmentioning

confidence: 99%

“…f C k * is the packing fraction: C k * = N ( V m / V c ), where N is the number of molecules in the unit cell, V m is the volume of the molecules in the unit cell (calculated with the program Platon 35 rather than using tables of incremental volumes, as done by Kitiagorodski), and V c is the total volume of the unit cell. g Lit . 309−310 °C.…”

Section: Introductionmentioning

confidence: 99%

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Engineering the Solid State with 2-Benzimidazolones

et al. 1996

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Six derivatives of 2-benzimidazolone, disubstituted in the 4 and 5 positions, have been synthesized, and their structures have been determined in the solid state. Four of these compounds crystallize as molecular tapes. Compounds 1-(CH3)2 , 1-Cl2 , and 1-Br2 form tapes that pack with their long axes parallel; compounds 1-H2 and 2-H2 form tapes that pack with their long axes at an angle to one another. Compounds 1-F2 and 1-I2 crystallize with a three-dimensional network of hydrogen bonds. The packing arrangement of molecular tapes is rationalized on the basis of closest packing and electrostatic interactions between aromatic rings. The occurrence of the network motif rather than the tape motif for 1-F2 and 1-I2 is rationalized on the basis of secondary interactions involving the halogen atoms.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Engineering the Solid State with 2-Benzimidazolones

et al. 1996

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“…The products were collected from a 6 ft 10% QF-1 CHROM H P 80/100 mesh column programmed in the same manner. Since starting material (6) does not elute from either column, it was recovered from a 6 ft 3% OV-1 CHROM H P 80/100 mesh column programmed between 100 and 250" at 1 S0/min a n d then held at 250" for 5 min.…”

Section: Pyrolysis Of 2-bet~zoxnzolinot~ementioning

confidence: 99%

“…mass spectrum of 2-benzothiazolinone (7) (5), and the e.i, mass spectrum of 2-benzoxazolinone (5) has been reported but not discussed (6). The 70eV e.i.…”

Section: Introductionmentioning

confidence: 99%

Pyrolyses and Mass Spectra of 2-Benzoxazolinone, 2-Benzimidazolinone, and 2-Benzothiazolinone

Thomson¹,

DeJongh²

1973

Can. J. Chem.

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The electron-impact and chemical-ionization mass spectra of 2-benzoxazolinone (5), 2-benzimidazolinone (6), and 2-benzothiazolinone (7) have been compared with their pyrolysis products and parallels have been found. In each case, loss of CO occurs from M t , followed by loss of C O for 5 and by H C N for 6 and 7. At 950" in a stream of N,, 5 gave 17% of C,H,N isomers, related to the loss of 2C0, along with 5.6% of quinoline. Compound 6gave 14% of C6H,N, isomers, related to the loss of CO. At 950°, 7 gave 2-thiophenecarbonitrile (1 .I%), cyanonaphthalenes (4.5%), sniline (373, cyanobenzene (2.5%), naphthalene (1.5%), and phenylisocyanate (2.5%). From 5-7 20-70% of the starting material was recovered or accounted for by isolation and identification of products in each case. G.c.1m.s. was used t o study pyrolysis mixtures.On rapporte les spectres de masse de la benzoxazolinone-2 (5), de la benzimidazolinone-2 (6) e t de la benzothiazolinone-2 (7). tels qu'obtenus par impact tlectronique et par ionisation chimique en utilisant I'isobutane. On compare ces spectres avec les produits de pyrolyse des coniposCs 5-7. Dans chaque cas, l'ion molCculaire elimine une molecule de CO. Pour les composCs 6 et 7, ce processus est suivi d'une elimination de HCN, alors que pour le compose 5, il est suivi de la perte d'une deuxieme molCcule d e CO.La pyrolyse du compost 5 a 950" dans un courant d'azote conduit a la formation de quinoline (5.6%) et d'isomeres repondant a la formule C5H,N, ces derniers a la suite de I'elimination de deux molecules de CO. Parallelement, le compose 6 donne des isomeres repondant a la formule C5H,N, ces derniers a la suite de I'Climination de deux molCcules de CO. Parallelement, le compose 6 donne des isomeres rdpondant a la formule C6H,N, par elimination d'une molCcule de C O et d'une molecule de HZ. Les produits de la pyrolyse du compose 7 a 950" sont le thiophknecarbonitrile-2 (1.1%), les cyanonaphthalenes (4.5%), I'aniline (373, le cyanobenzene (2.5%), le naphthalene (1.5%) et I'isocyanate de phenyle (2.5%). Les produits form& ainsi que les produits originaux rCcupCrCs representent de 20 a 70% des produits de depart. La combinaison de la chromatographie en phase gazeuse avec la spectrometrie de masse etait employee pour Ctudier les melanges obtenus des pyrolyses.

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“…Recently it was reported that alkylation of benzoxazol-2(3H)-ones and benzothiazole-2(3H)-ones gave the intermediates, which are used in pharmacotherapy for their anticocaine activity, as these 75 substituted heterocycles interact with signal receptors. Consequently, numerous methods such as Hofmann rearrangement of amides, 35 carbonylation of o-substituted aryl azides using Rhodium catalyst, 36 two steps cyclization of ohydroxybenzoic acids, 37 cyclization of arenecarbohydroxamic 80 acid, 38 photochemical rearrangements of 1,2-benisoxazolinones, 39 cyclization of azidoformates 40 have been developed for the synthesis of benzoxazol-2(3H)-one derivatives. Among them, the cyclization of o-aminophenols with various carbonylating reagents such as, 1,1-carbonyldimidazole, 41 chloroformates, 42 85 alkyl carbonates, 43 triphosgene, 44 pentafluorobenzoyl chloride 45 are the most commonly used reagents for the synthesis of benzoxazol-2(3H)-ones.…”

Section: Introductionmentioning

confidence: 99%

General and efficient synthesis of benzoxazol-2(3H)-ones: evolution of their anti-cancer and anti-mycobacterial activities

et al. 2014

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A novel class of benzo [d]oxazol-2(3H)-one derivatives have been synthesized and evaluated their in vitro cytotoxicity against human pancreatic adenocarcinoma and human non small cell lung carcinoma cancer cell lines. Many of these compounds were found to display excellent to moderate activity. Among them, 6b, 6l, 6n and 6x are identified as lead molecules. In particular, 6l and 6n were found to be potent against 10 pancreatic cell line whereas the 6x was found to be effective against human non small cell lung carcinoma cell line. Conversely, the compounds 6l-x were found to ineffective against Mycobacterium tuberculosis. Of various molecules, 6h showed a promising anti-mycobacterial activity, which is equal to the IC 50 value of ciprofloxacin. Off White solid; 92% yield, m.p. 216-218 o C; 1 H NMR (400 MHz, DMSO): δ 10.35 (s, 1H), 8.41 (d, J = 7.2 Hz, 2H), 8.04 (s, 1H), 8.19 (d, J = 7.0 Hz, 2H), 7.59 (d, J = 8.2 Hz, 2H), 7.57 (m, 1H), 7.52 (s, 1H), 7.45 (m, 4H), 4.52 (m, 1H), 1.51 (d, J = 6.8 Hz, 6H);

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Synthesis of fused azolones from ortho-substituted arenecarbohydroxamic acids

Cited by 25 publications

References 1 publication

Engineering the Solid State with 2-Benzimidazolones

Engineering the Solid State with 2-Benzimidazolones

Pyrolyses and Mass Spectra of 2-Benzoxazolinone, 2-Benzimidazolinone, and 2-Benzothiazolinone

General and efficient synthesis of benzoxazol-2(3H)-ones: evolution of their anti-cancer and anti-mycobacterial activities

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