Cationic 2-Azabutadienes from α-Arylaminosulfones and α-Arylaminonitriles: Intermolecular Polar [4π+ + 2π]-Cycloadditions for the Regio- and Diastereoselective Synthesis of 1,2,3,4-Tetrahydroquinolines

Synlett

Volumn 1996, Issue 1, 1996, Pages 34-36

  Beifuss, Uwe ^a   Kunz, Olaf ^a   Ledderhose, Sabine ^a   Taraschewski, Michael ^a   Tonko, Christiane ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002970329     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5305     Document Type: Article

References (41)

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31. 13C NMR, IR, UV, and mass spectra. The elemental analyses and/or high-resolution mass spectrometric data are consistent with the calculated data. The yields refer to analytically pure compounds.
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35. General Experimental Procedure the the synthesis of 4: Aqueous 37% formaldehyde (2) (1.02 mmol) and a solution of the appropriate aniline 1 (1.00 mmol) in methanol (1 mL) was added, one after the other, to a solution of p-toluenesulfinic acid (3) in methanol (1.00 mL) at 0 °C and the reaction mixture was stirred at room temperature for the time given in Table 1. After precipitation the crystalline aminosulfone 4 was filtered with suction, washed with ice cold water, and dried in vacuo.
36. 2 at -78 °C. After 10 min ut -78 °C the dienophile 5, 7, 9, or 11 was added dropwise, the solution was stirred at -78 °C until completion (TLC) and then warmed up to room temperature. The reaction was quenched by addition of saturated sodium hydrogencarbonate (10 mL). After extraction with dichloromethane (3 x 10 mL) the combined organic layers were dried over sodium sulfate, the solvent was removed in vacuo and the residue was purified by column chromatography on silica gel.
37. HX), 6.40-6.46 (m, 2H, 6-H, 7-H), 6.64 (d, J = 8.0 Hz, 1H, 8-H), 6.94-7.32 (m, 6H, 5-H, 2′-H, 3′-H, 4′-H, 5′-H, 6′-H);
38. ax), 6.47 (dt, J = 1.0 Hz, J = 7.5 Hz, 1H, 6-H), 6.67 (dd, J = 1.0 Hz, J = 8.0 Hz, 1H, 8-H), 6.74 (dd, J = 2.0 Hz, J = 7.5 Hz, 1H, 5-H), 6.95-7.29 (m, 6H, 7-H, 2′-H, 3′-H, 4′-H, 5′-H, 6′-H).
39. Calculations were performed using the VAMP and MOPAC 6.0 packages. VAMP (T. Clark, Universität Erlangen-Nürnberg) is a vectorized version of AMPAC and MOPAC.
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