SCOPUS 정보 검색 플랫폼

Volumn , Issue 5, 2007, Pages 821-823

A novel three-component, one-pot synthesis of 1,2-dihydro-1-aryl-naphtho[1, 2-e][1,3]oxazine-3-one derivatives under microwave-assisted and thermal solvent-free conditions

(3) Dabiri, Minoo a Delbari, Akram Sadat a Bazgir, Ayoob a

a SHAHID BEHESHTI UNIVERSITY (Iran)

Author keywords

Microwave; Multi component; Naphthol; Naphthoxazinone; Solvent free

Indexed keywords

1,2 DIHYDRO 1 ARYL NAPTHO[1,2 E][1,3]OXAZINE 3 ONE DERIVATIVE; 2 NAPHTHOL; ALDEHYDE DERIVATIVE; OXAZINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICROWAVE RADIATION; POLYMERIZATION; SYNTHESIS;

EID: 33947730183 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-970763 Document Type: Article

Times cited : (89)

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- 2O and then recrystallized from EtOAc-hexane (1:3) to afford the pure product 4a as a white powder (58%).
- 2O and then recrystallized from EtOAc-hexane (1:3) to afford the pure product 4a as a white powder (58%).

24
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- Typical procedure under microwave-assisted conditions: A mixture of β-naphthol (1 mmol, benzaldehyde (1 mmol) and urea (1.5 mmol) were finely mixed together. The reaction mixture was placed in a screw-capped vial and irradiated for 6 min with a power of 900 W. After cooling, the reaction mixture was washed with H2O and then recrystallized from EtOAc-hexane (1:3) to afford the pure product 4a (81, mp 218-220°C; IR (KBr, 3295, 1730, 1517 cm-1; 1H NMR (300 MHz, DMSO-d 6, δ, 6.19 (d, J, 2.1 Hz, 1 H, CH, 7.24-8.00 (m, 11 H, Ar-H, 8.87 (br s, 1 H, NH, 13C NMR (75 MHz, DMSO-d 6, δ, 54.20, 114.50, 117.32, 123.57, 125.54, 127.42, 127.81, 128.47, 129.08, 129.32, 129.41, 130.68, 130.86, 143.34, 147.85, 149.77; MS (ESI, m/z, 275 (7, M, 231 (100, 202 (35, 51 24
- +], 231 (100), 202 (35), 51 (24).

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29
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- Selected characterization data: 1,2-Dihydro-1-(4-methylphenyl) naphtho[1,2-e][1,3]oxazine-3-one (4b, mp 166-16°C; IR (KBr, 3230, 3139, 1717 cm-1; 1H NMR (300 MHz, DMSO-d 6, δ, 2.21 (s, 3 H, CH3, 6.13 (d, J, 2.4 Hz, 1 H, CH, 7.10-7.99 (m, 10 H, Ar-H, 8.81 (s, 1 H, NH, 13C NMR (75 MHz, DMSO-d6, δ, 21.06, 53.98, 114.61, 117.29, 123.56, 125.49, 127.32, 127.76, 129.05, 129.33, 129.89, 130.59, 130.85, 137.78, 140.43, 147.80, 149.81; MS (ESI, m/z, 290 (10, M, H, 231 (100, 202 (20, 1,2-Dihydro-1-(4-chlorophenyl)naphtho[1,2- e][1,3]oxazine-3-one(4f, mp 208-210°C; IR (KBr, 3224, 3146, 1734 cm-1; 1H NMR (300 MHz, DMSO-d 6, δ, 6.24 (s, 1 H, CH, 7.31-8.01 (m, 10 H, Ar-H, 8.91 (s, 1 H, NH, 13C NMR 75 MHz, DMSO-d6, δ, 53.42, 114.02, 11
- 3], 231 (100), 202 (15), 144 (100).

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