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Volumn , Issue 20, 2006, Pages 3431-3434

Recyclization of hydrazides of 2-carboxyphenyldifurylmethanes: Synthesis of novel 4,10-dihydro-3H-pyridazino[1,6-b]isoquinolin-10-one system

(4) Butin, Alexander V a Dmitriev, Artem S a Abaev, Vladimir T b Zavodnik, Valery E c

a KUBAN STATE TECHNOLOGICAL UNIVERSITY (Russian Federation)

b NORTH OSSETIAN STATE UNIVERSITY (Russian Federation)

c KARPOV INSTITUTE OF PHYSICAL CHEMISTRY (Russian Federation)

Author keywords

Furans; Fused ring systems; Pyridazino 1,6 b isoquinolin 10 one; Ring closure; Ring opening

Indexed keywords

2 CARBOXYPHENYLDIFURYLMETHANE DERIVATIVE; 4,10 DIHYDRO 3H PYRIDAZINOL[1,6 B]ISOQUINOLIN 10 ONE; HYDRAZIDE DERIVATIVE; HYDRAZINE; ISOCOUMARIN DERIVATIVE; ISOQUINOLINE DERIVATIVE; KETONE DERIVATIVE; METHANE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; SYNTHESIS;

EID: 33846485628 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2006-958419 Document Type: Article

Times cited : (7)

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21
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22
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- 2O (300 mL)

23
- 33846512213
- Preparation of Compounds 13a-f (Method A, General Procedure To a 15% solution of p-TsOH in benzene (20 mL, prepared by refluxing p-TsOH·H2O in benzene with azeotropic removal of H 2O, compound 10 (4.19 mmol) was added and the mixture was refluxed for 10 min. The resulting solution was poured into H2O (300 mL, The slurry was extracted with CH2Cl2 (3 × 50 mL, The combined extract was washed with H2O, dried over anhyd Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel (hexane-EtOAc, 4:1, Solvent was stripped off of the eluate and the residue was recrystallized from hexane-EtOAc (10:1) at temperature below 0 °C. Selected analytical data of 13b: mp 173-174 °C. IR: 1667 (CO) cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.33 (s, 3 H, CH3, 2.33 t, J, 7.5 Hz, 2 H, CH
- 2: C, 66.16; H, 4.63. Found: C, 66.08; H, 4.69.

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31
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- 4 and evaporated to dryness. The residue was purified by column chromatography on silica gel (hexane-EtOAc, 4:1). The solvent was stripped off of the eluate and the residue was recrystallized from hexane-EtOAc (10:1) at temperature below 0 °C.
- 4 and evaporated to dryness. The residue was purified by column chromatography on silica gel (hexane-EtOAc, 4:1). The solvent was stripped off of the eluate and the residue was recrystallized from hexane-EtOAc (10:1) at temperature below 0 °C.

32
- 33846517583
- Crystal data of compound 13f: C18H15BrN 2O2, monoclinic, space group C2/c; a, 32.028(6) Å, b, 11.022(2) Å, c, 9.016(2) Å, α, 90°, β, 90.48(3)°, γ, 90°, V, 3182.6(11) Å3= 8, D calcd, 1.550 Mg/m3, F(000, 1504; 3330 reflections collected, 3116 unique (Rint, 0.0269, final R indices (3116 observed collections I > 2σI, R1, 0.0331, wR2, 0.0818; final R indices (all data, R1, 0.1677, wR2, 0.0945. Crystallographic data (excluding structure factors) for the structure in this article have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 614755. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or E-mail: deposit@ccdc.cam.ac.uk, Each request s
- 2 = 0.0945. Crystallographic data (excluding structure factors) for the structure in this article have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 614755. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or E-mail: deposit@ccdc.cam.ac.uk]. Each request should be accompanied by the complete citation of this paper.

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