Preparation of 7<i>H</i>‐dibenzo[<i>de, g</i>]quinol‐7‐ones (“7‐oxoaporphines”)

Cannon, Joseph G.; Kim, Jack C.; Aleem, Mohd

doi:10.1002/jhet.5570090346

Cited by 9 publications

(5 citation statements)

References 10 publications

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“…yield 55% (63.5 mg, 0.275 mmol); yellow solid; mp 222–224 °C (lit . mp 222–222.5 °C); 1 H NMR (600 MHz, CDCl 3 ) δ 7.60 (1H, t, J = 7.8 Hz), 7.78 (1H, td, J = 7.8, 1.2 Hz), 7.87 (1H, t, J = 7.8 Hz), 7.98–8.00 (2H, m), 8.30 (1H, d, J = 7.8 Hz), 8.45 (1H, d, J = 7.8 Hz), 8.56 (1H, dd, J = 7.8, 1.2 Hz), 9.06 (1H, d, J = 5.4 Hz); 13 C NMR (150 MHz, CDCl 3 ) δ 123.1, 124.5, 124.6, 125.1, 128.6, 128.7, 129.1, 129.2, 131.0, 131.6, 134.1, 134.9, 136.9, 145.5, 146.7, 182.7; IR (KBr) 1665 cm –1 ; EIMS m / z (rel int) 231 (100, M + ); HREIMS m / z calcd for C 16 H 9 NO 231.0684, found 231.0686 [M] + .…”

Section: Methodsmentioning

confidence: 99%

“…yield 61% (88.8 mg, 0.305 mmol); orange solid; mp 179–180 °C (lit . mp 190–191 °C); 1 H NMR (500 MHz, CDCl 3 ) δ 4.12 (3H, s), 4.18(3H, s), 7.55 (1H, t, J = 7.9 Hz), 7.74 (1H, t, J = 7.9 Hz), 8.14–8.17 (2H, m), 8.22 (1H, d, J = 5.6 Hz), 8.51 (1H, d, J = 7.9 Hz), 8.97 (1H, d, J = 5.6 Hz); 13 C NMR (125 MHz, CDCl 3 ) δ 57.1, 61.7, 113.9, 119.1, 120.8, 122.6, 125.3, 128.7, 129.0, 131.3, 133.2, 133.8, 134.5, 143.5, 145.2, 146.3, 151.2, 182.8; IR (KBr) 1667 cm –1 ; EIMS m / z (rel int) 291 (100, M + ); HREIMS m / z calcd for C 18 H 13 NO 3 291.0895, found 291.0888 [M] + .…”

Section: Methodsmentioning

confidence: 99%

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Direct Conversion of 1-(2-Bromobenzoyl)isoquinolines to Dibenzo[de,g]quinolin-7-ones via Reductive Photocyclization

Chuang

Lee

et al. 2013

J. Org. Chem.

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A series of A/D-ring substituted dibenzo[de,g]quinolin-7-ones was produced from the corresponding isoquinolinones and (2-bromophenyl)acetonitriles in four steps. This represents a convenient approach toward the synthesis of tetracyclic alkaloids. A direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[de,g]quinolin-7-ones is the key step in the total synthesis. The yield of the reductive photocyclization depends on the position of the substituents at the isoquinolyl ring and the phenyl group. The mechanism of the reductive photocyclization is also discussed.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Direct Conversion of 1-(2-Bromobenzoyl)isoquinolines to Dibenzo[de,g]quinolin-7-ones via Reductive Photocyclization

Chuang

Lee

et al. 2013

J. Org. Chem.

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“…The residual oil crystallized after the addition of water. Recrystallization of this solid from benzene-hexane gave 5a (2.44 g,46%): mp 124-125 "C;'H NMR 6 o-(p-Ch1orophenoxy)phenylacetic acid (5b) was prepared from 7b as described for the preparation of 5a from 7a and was recrystallized from benzene-hexane (66%): mp 120-121 "C (lit.lo mp 115-118 "C); lH NMR 6 3.72 (s, 2, CH2C02), 6.78-7.30 (m, 8, aromatic H), 10.80 (br s, 1, C02H). o -Phenoxyphenylacetic Acid (5c) and 2-Morpholino-2-t hioxo-1-( o -phenoxyphenyl)-1-et hanone (1Oc).…”

Section: -Chloro-loll-dihydrodibenz[b F]oxepin-10-one (4b) Wasmentioning

confidence: 99%

“…After the ether was evaporated, recrystallization of the solid residue from toluene gave 9 (0.63 g, 91%): mp 177-178 "C (lit.13 mp 175 "C); 'H NMR 6 Biological Activity. Brain tissue and other materials for biological testing were as reported earlier.…”

Section: -Morpholino-2-(o -Phenoxyphenyl)-1-ethanethione (812)mentioning

confidence: 99%

Affinity of 10-(4-methylpiperazino)dibenz[b,f]oxepins for clozapine and spiroperidol binding sites in rat brain

Tw¹,

He²,

Pl³

et al. 1982

J. Med. Chem.

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10-(4-Methylpiperazino)dibenz[b,f]oxepins were prepared and evaluated as potential antipsychotic agents using specific clozapine [8-chloro-11-(4-methylpiperazino)-5H-dibenzo[b,e][1,4]diazepine] binding sites in rat forebrain that are noncholinergic and nondopaminergic in nature and from which [3H]clozapine is displaced by known antipsychotic agents. [3H]Clozapine binding in the presence of atropine represents nonmuscarinic binding, while binding in the absence of atropine represents muscarinic (cholinergic) plus nonmuscarinic binding. The relative affinity for dopamine binding sites was determined by displacement of [3H]spiroperidol from binding sites in rat caudate nuclei. Thus, clozapine, its 2-chloro isomer, its dechloro analogue, and their 5H-dibenzo[a,d]cycloheptene and dibenz[b,f]oxepine analogues have about the same relative affinity for the nonmuscarinic clozapine binding sites. At the spiroperidol (dopaminergic) sites, both the nature of the tricyclic system and the presence of a chlorine atom on the tricyclic system have a substantial effect on the binding affinity. Within each series, shift or a chlorine atom from the position distal to the piperazino group to the proximal position increases the binding affinity by a factor of about nine, but removal of the chlorine atom substantially decreases the binding affinity. Nevertheless, 10-(4-methylpiperazino)dibenz[b,f]oxepin has a threefold greater affinity for the dopaminergic binding sites than does clozapine itself.

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“…While such an approach has found considerable application in the areas of cholinergic agonists (1)(2)(3)(4)(5), on phenethanolamine systems (6-ll), and dopaminergic agonists (12), relatively few examples of conformationally defined analogs of amphetamine have been reported and definite structure-activity relationships are noticeably scant.…”

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confidence: 99%

Conformationally defined adrenergic agents I: Potentiation of levarterenol in rat vas deferens by endo- and exo-2-aminobenzobicyclo[2.2.2]octenes, conformationally defined analogs of amphetamine

Grunewald

Ruth

Kroboth

et al. 1976

Journal of Pharmaceutical Sciences

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Preparation of 7H‐dibenzo[de, g]quinol‐7‐ones (“7‐oxoaporphines”)

Cited by 9 publications

References 10 publications

Direct Conversion of 1-(2-Bromobenzoyl)isoquinolines to Dibenzo[de,g]quinolin-7-ones via Reductive Photocyclization

Direct Conversion of 1-(2-Bromobenzoyl)isoquinolines to Dibenzo[de,g]quinolin-7-ones via Reductive Photocyclization

Affinity of 10-(4-methylpiperazino)dibenz[b,f]oxepins for clozapine and spiroperidol binding sites in rat brain

Conformationally defined adrenergic agents I: Potentiation of levarterenol in rat vas deferens by endo- and exo-2-aminobenzobicyclo[2.2.2]octenes, conformationally defined analogs of amphetamine

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