High pressure promoted tandem [4+2]/[3+2] cycloadditions on the solid phase

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3613-3616

  Kuster, George J ^a   Scheeren, Hans W ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

High pressure synthesis; Nitroso compounds; Solid phase synthesis; Tandem 4+2 3+2. cycloaddition

Indexed keywords

ALKENE DERIVATIVE; NITROSOACETAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; ESTERIFICATION; REACTION ANALYSIS; SOLID STATE; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032554999     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00563-2     Document Type: Article

References (17)

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12. Without a Lewis acid catalyst, an additional activating electron withdrawing substituent on the nitrostyrene is required (in the [4+2] cycloaddition): Tohda Y, Yamawaki N, Matsui H, Kawashima T, Ariga M, Mori Y. Bull. Chem. Soc. Jpn. 1988;61:461-465.
13. 2 (3x 10 mL). The resin was dried at 70°C under reduced pressure for 2 h. The increase in weight of the resin was a measure of the amount of cycloadduct formed on the resin. For less substituted enol ethers and nitrostyrenes good conversions were already achieved at lower pressures and shorter reaction times (12 kbar, 17 h). We have chosen the given standard conditions (15 kbar, 48 h) because of satisfactory conversions using more substituted reaction partners.
14. In the case of 2b (entry d, e and f) the C-N signal is probably hidden under neighbouring frequencies of the resin.
15. 5: 361.1889, found 361.1890 ±0.0014.
16. Synthesis of 1-methoxy-1-cyclohexene is described in Houben Weil, E 15/Teil 1:268 Georg Thiemes Verlag Stutgart-New York.
17. These compounds are studied in the framework of our research towards CNS active compounds related to serotonin and dopamin.