Polarisation der heterozyklischen Ringe mit aromatischem Charakter. CXVII. Synthetische Versuche des Dehydronoraporphins.

Ochiai, Eiji; Kuniyoshi, Ieji

doi:10.1248/cpb1953.5.292

Cited by 5 publications

(3 citation statements)

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“…Yield 97% (2.19 g, 6.8 mmol); white needle; mp 160–161 °C (hexane–EtOAc) (lit . mp 152.5 °C); 1 H NMR (500 MHz, CDCl 3 ) δ 6.52 (1H, s), 7.21 (1H, td, J = 7.8, 1.7 Hz), 7.27 (1H, td, J = 7.8, 1.7 Hz), 7.41 (1H, dd, J = 7.8, 1.7 Hz), 7.60–7.63 (1H, m), 7.65 (1H, dd, J = 7.8, 1.7 Hz), 7.69–7.72 (2H, m), 7.89 (1H, d, J = 8.2 Hz), 7.97 (1H, d, J = 8.2 Hz), 8.61 (1H, d, J = 5.7 Hz); 13 C NMR (125 MHz, CDCl 3 ) δ 42.2, 177.7, 121.5, 123.4, 123.7, 125.5, 127.7, 128.2, 128.3, 130.2, 130.3, 130.4, 133.1, 134.2, 136.6, 141.9, 153.0; IR (KBr) 2249 cm –1 ; ESIMS m / z (rel int) 323 (100, [M + 1] + ), 323 (100, [M + 3] + ).…”

Section: Methodsmentioning

confidence: 99%

“…(2-Bromophenyl)isoquinolin-1-ylacetonitrile (12a): Yield 97% (2.19 g, 6.8 mmol); white needle; mp 160−161 °C (hexane− EtOAc) (lit. 44 2,177.7,121.5,123.4,123.7,125.5,127.7,128.2,128.3,130.2,130.3,130.4,133.1,134.2,136.6,141.9,153.0;IR (KBr) 13 C NMR (125 MHz, CDCl 3 ) δ 41.8, 55. 9,56.1,112.4,113.5,115.3,118.1,121.5,123.9,125.6,126.0,127.7,128.3,130.5,136.7,141.9,149.1,149.9,153.5;IR (KBr) 2,109.8,112.8,114.2,117.9,121.6,123.8,125.6,127.3,127.8,128.4,130.5,136.8,142.0,148.1,148.8,153.3;IR (KBr) 13 C NMR (125 MHz, CDCl 3 ) δ 41.7, 117.3, 121.9, 123.2 (q, J = 271 Hz), 123.4, 125.7, 126.9 (q, J = ...…”

Section: ■ Experimental Sectionmentioning

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: ■ Experimental Sectionmentioning

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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show abstract

“…cis-10,10-Dimethylbicyclo[6.2.0]decan-9-one (15) obtained from the hydrolysis of 9 showed indeed the two net ir absorptions at 1462 and 1450 cm-1 which appear to be typical for an eight-membered ring cis fused to threeor four-membered rings. 7 The protons of the ge/n-dimethyl groups gave two singlets ( 1.23 and 0.93). On the other hand, trans-10,10dimethylbicyclo[6.2.0]decan-9-one (16) obtained from the hydrolysis of 10 showed only one signal for the six methyl protons at 1.08.…”

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confidence: 98%