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Volumn , Issue 8, 2007, Pages 1305-1307

Synthesis of 7,8-benzo-4-hydroxy-1,9-diazabicyclo[3.3.1]non-3-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazoline

b NONE

Author keywords

Cyclizations; Iminium salts; N heterocycles; Quinazolines; Silyl enol ethers

Indexed keywords

1,3 BIS(SILYL ENOL ESTHER DERIVATIVE); 7,8 BENZO 4 HYDROXY 1,9 DIAZABICYCLO[3.3.1]NON 3 ENE DERIVATIVE; QUINAZOLINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 34249824279 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-977443 Document Type: Article

Times cited : (17)

References (14)

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- Scriven, E. F. V. Pyridines and their Benzo Derivatives:(ii) Reactivity at Ring Atoms, In Comprehensive Heterocyclic Chemistry, Vol. 2, Part 2A; Boulton, A. J.; McKillop, A.; Katritzky, A. R.; Rees, C. W., Eds.; Elsevier Science: Oxford, 1984, Chapt. 2.05, 165.

2
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- Rudler, H.¹ Denise, B.² Parlier, A.³ Daran, J.-C.⁴

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- Ullah, E.; Rotzoll, S.; Schmidt, A.; Michalik, D.; Langer, P. Tetrahedron Lett. 2005, 46, 8997.
- (2005) Tetrahedron Lett , vol.46 , pp. 8997
- Ullah, E.¹ Rotzoll, S.² Schmidt, A.³ Michalik, D.⁴ Langer, P.⁵

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7
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- (a) Schmidt, A.; Gütlein, J.-P.; Preuss, A.; Albrecht, U.; Reinke, H.; Langer, P. Synlett 2005, 2489.
- (2005) Synlett , pp. 2489
- Schmidt, A.¹ Gütlein, J.-P.² Preuss, A.³ Albrecht, U.⁴ Reinke, H.⁵ Langer, P.⁶

8
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9
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12
- 34249775597
- General Procedure for the Cyclization of Quinazolines with 1,3-Bis(silyl enol ethers) To a CH2Cl2 soln (40 mL) of quinazoline (0.521 g, 4.0 mmol) was added the 1,3-bis(silyl enol ether, 5.6 mmol) and methyl chloroformate (1.512 g, 16.0 mmol) at 0°C. The solution was stirred for 2 h at 0°C and for 12 h at 20°C. The solvent was removed in vacuo. The residue was purified by chromatography (silica gel, heptane → heptane-EtOAc, 2:1, Synthesis of 3a Starting from quinazoline (0.521 g, 4.0 mmol, 2a (1.460 g, 5.6 mmol) and methyl chloroformate (1.512 g, 16.0 mmol, 3a was obtained as a colorless solid (0.750 g, 52, 1H NMR (250 MHz, CDCl3, δ, 2.41 (dd, 2J, 17.5 Hz, 3J, 1.5 Hz, 1 H, CH 2, 2.99 (br dd, 1 H, CH2, 3.76 (s, 3 H, OCH 3, 3.80 (s, 3 H, OCH3, 3.87 (s, 3 H, OCH3, 5.40 br, 1 H, NCHCH
- 7 (362.33): C, 56.35; H, 5.01; N, 7.73. Found: C, 56.35; H, 5.13; N, 7.46.

13
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- (2006) Tetrahedron , vol.62 , pp. 12351
- Chilin, A.¹ Marzaro, G.² Zanatta, S.³ Barbieri, V.⁴ Pastorini, G.⁵ Manzini, P.⁶ Guiotto, A.⁷

14
- 34249788233
- CCDC-617334 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk.
- CCDC-617334 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk.

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