A three-component approach to isoquinoline derivatives by cycloaddition/Heck reaction sequence

Tetrahedron Letters

Volumn 48, Issue 24, 2007, Pages 4255-4258

  Oikawa, Masato ^a   Takeda, Yoshiyuki ^a   Naito, Shinya ^a   Hashizume, Daisuke ^b   Koshino, Hiroyuki ^b   Sasaki, Makoto ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CHLORMETHINE N OXIDE; ISOQUINOLINE DERIVATIVE; MALEIMIDE; PALLADIUM;

ARTICLE; CYCLIZATION; CYCLOADDITION; DIASTEREOISOMER; DRUG SYNTHESIS; HECK REACTION; POLYMERIZATION; THERMODYNAMICS;

EID: 34248592231     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.082     Document Type: Article

References (18)

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8. Prepared from 2-but-3-enyl chloride and N-hydroxyphthalimide over 2 steps (34% yield) by a reported procedure, see:. Irie H., Katayama I., Mizuno Y., Koyama J., and Suzuta Y. Heterocycles 12 (1979) 771-773
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10. 1H J-coupling constants and NOESY experiments, and finally confirmed by X-ray diffraction analysis of 21α.
11. Oxime O-allylic ethers 14 and 16 were prepared from 2-bromo-3-hydroxy-4-methoxybenzaldehyde over 4 and 5 steps for 60% and 46% yields, respectively.
12. 1H J-coupling constants and NOESY experiments, and finally confirmed by analogy with the synthesis of 21α.
13. Prepared from 2-iodobenzaldehyde as for 13 shown in Scheme 2 over 2 steps (66% yield).
14. The crystallographic data for 21α have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number, CCDC 620027. Dihydroisoquinoline 21α has been also recently synthesized by an alternative four-component coupling approach, see:. Dondas H.A., Fishwick C.W.G., Gai X.J., Grigg R., Kilner C., Dumrongchai N., Kongkathip B., Kongkathip N., Polysuk C., and Sridharan V. Angew. Chem., Int. Ed. 44 (2005) 7570-7574
15. The details will be reported in the full account of this research.
16. Calculated on BARISTA software (BARISTA, version 1.2.2; CONFLEX Co., Yotsuya 4-30, Shinjuku-ku, Tokyo 160-0004, Japan).
17. A considerable amount (30%) of the trisubstituted, olefin isomer of 27α was also detected in the Heck cyclization of 24.
18. In the cases for the synthesis of 28α and 29α, unreacted β-isomer of 25 (33%) and 26 (33%) were recovered after the reaction, indicating these β-isomers are less reactive than the α-isomer. Because prolonged reaction was found to cause decomposition from the experiment of 20, we are currently optimizing the other reaction conditions for this transformation.