REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .9. SYNTHESIS OF MEDIUM-SIZE AZAHETEROCYCLES

Citation
Eg. Occhiato et al., REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .9. SYNTHESIS OF MEDIUM-SIZE AZAHETEROCYCLES, Gazzetta chimica italiana, 123(8), 1993, pp. 425-429
Citations number
19
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
ISSN journal
0016-5603
Volume
123
Issue
8
Year of publication
1993
Pages
425 - 429
Database
ISI
SICI code
0016-5603(1993)123:8<425:ROID.S>2.0.ZU;2-8
Abstract
1,3-dipolar cycloaddition of benzonitrile oxide, 1, to 3-methyl-2,3,5, 6-tetrahydro-7(1H)-indolizinone, 9, afforded the unexpected tetracycli c adduct 12. The crystal structure of compound 12 has been determined by single crystal X-ray diffraction analysis. The compound crystallize s in the orthorhombic space group Pbna, with a = 11.208(3), b = 17.526 (2) and c = 19.392(2) angstrom, V = 3809(1) angstrom3, Z = 8. The stru cture was solved by means of direct methods and refined by full-matrix least-squares calculations to R = 0.045 and R(w) = 0.041. Reductive c leavage of the isoxazoline N-O bond in 12 allowed enlargement of the r ing by cleavage of the C-N bridge bond, to afford, in 68% yield, an az onine derivative having the tautomeric structures 15 or 16.