Iodo-cyclization of N-Homoallyl thioamides leading to 2,4-Diaryl-5,6- dihydro-4H-1,3-thiazines

Chemistry Letters

Volumn 33, Issue 5, 2004, Pages 508-509

  Murai, Toshiaki ^a   Niwa, Hisayuki ^a   Kimura, Tsutomu ^a   Shibahara, Fumitoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CARBON; NITROGEN; PROLINE DERIVATIVE; THIAZINE DERIVATIVE; THIOAMIDE;

ALLYLATION; ARTICLE; ARYLATION; ATOM; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 3242757492     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.508     Document Type: Article

References (21)

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15. Iodo-cyclization of N-3-butenyl thiourea has been reported to form 2-amino-5,6-dihydro-5-iodoalkyl-4H-1,3-thiazine, but the reaction conditions have not been shown: P. I. Creeke and J. M. Mellor, Tetrahedron Lett., 30, 4435 (1989).
16. 4, filtered, and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to give 2.
17. 22INOS: C, 53.22; H, 4.91, N, 3.10. Found: C, 53.05; H, 4.84; N, 3.08%.
18. Although the result in Entry 5 is not completely understood at the present stage, the interaction of the iodine atom with the oxygen atom of MeO group may be present in the iodonium ion intermediate.
19. w = 0.096, 7800 reflections (I > 2σ(I)).
20. w = 0.142, 4352 reflections (I > 2σ(I)).
21. Only one example of 6-alkylidene-5,6-dihydro-4H-1,3-thiazines is reported. T. Hirayama, S. Fukatsu, A. Seki, H. Goi, and Y. Yamada, JP 53111080; Chem. Abstr., 90, 103982.