SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 2, 2009, Pages 201-204

First synthesis of functionalized benzonitriles by formal [3+3] cyclocondensations of 1,3-bis(silyloxy)buta-1,3-dienes

(6) Fatunsin, Olumide a Shkoor, Mohanad a Riahi, Abdolmajid a Dede, Rüdiger a Reinke, Helmut a Langer, Peter a

a UNIVERSITY OF ROSTOCK (Germany)

Author keywords

Arenas; Benzonitriles; Cyclizations; Regioselectivity; Silyl enol ethers

Indexed keywords

EID: 62349138305 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087395 Document Type: Article

Times cited : (3)

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- Typical Experimental Procedure for the Synthesis of 4a-l To a stirred solution of CH2Cl2 (3 mL per 1.0 mmol of 2a-e) of 2a-e was added 3a-h (1.1 mmol) and, subsequently, TiCl4 (1.1 mmol) at -78°C under argon atmosphere. The temperature of the reaction mixture was allowed to rise to 20°C over 14 h with stirring. To the solution was added HCl (10, 20 mL) and the organic and the aqueous layer were separated. The latter was extracted with CH 2Cl2 (3 x 20 mL, The combined organic layers were dried (Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptanes-EtOAc) to give 4a-l. Starting with 2a (0.209 g, 1.5 mmol) and 3a (0.446 g, 1.65 mmol, 4a was isolated as a colorless solid (101 mg, 33, mp 86-87°C. 1H NMR 250 MHz, CDCl3, δ, 1.39
- 3: 205.07334; found: 205.073572.

50
- 62349124922
- CCDC-703181 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, CB2 1EZ, UK; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk.
- CCDC-703181 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, CB2 1EZ, UK; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk.

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52
- 62349120302
- Typical Experimental Procedure for the Synthesis of 6a-f To a CH2Cl2 solution of 5 was added TiCl4 at -78°C in the presence of MS (4 Å, The appropriate bis(silyl enol ether) 3 was subsequently added. The reaction mixture was allowed to warm to 20°C during 20 h and was stirred for further 4 h. To the solution was added CH2Cl2, the MS were removed, and a sat. aq soln of NaHCO3 was added. The organic layer was separated, and the aqueous layer was repeatedly extracted with CH2Cl2. All organic extracts were combined, dried (Na2SO4, and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2) to give salicylates 6. Starting with 5 (188 mg, 0.95 mmol, CH2Cl2 (3.0 mL, MS (4 Å, 0.4 g, TiCl4 (0.11 mL, 1.0 mmol, and 3i 356 mg, 1
- 3 (205.21): C, 64.38; H, 5.40; N, 6.83. Found: C, 64.64; H, 5.52; N, 6.65.

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