Products from a novel reaction of dihydropyrazines with vichinaldiamines

Heterocycles

Volumn 51, Issue 10, 1999, Pages 2305-2309

  Yamaguchi, Tadatoshi ^a   Ito, Shigeru ^b   Iwase, Yukiko ^c   Watanabe, Kenji ^c   Harano, Kazunobu ^d  

^a UNIVERSITY OF MIYAZAKI   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^c FUKUOKA UNIVERSITY   (Japan)

^d KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DECALIN DERIVATIVE; DIAMINE DERIVATIVE; PYRAZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE;

EID: 0033214829     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-8678     Document Type: Article

References (14)

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2. T. Yamaguchi, M. Eto, K. Watanabe, N. Kashige, and K.Harano, Chem. Pharm. Bull., 1996, 44, 1977.
3. T. Yamaguchi, M. Eto, K. Harano, N. Kashige, K. Watanabe, and S. Ito, Tetrahedron, 1999, 55, 675.
4. T. Yamaguchi, N. Kashige, S. Matsumoto, K. Satoh, M. Yasuda, and K. Watanabe, Biol. Pharm. Bull., 1998, 21, 205.
5. T. Yamaguchi, S. Matsumoto, and K. Watanabe, Tetrahedron Lett., 1998, 39, 8311.
6. H. Stetter, Chem. Ber., 1953, 86, 69.
7. B. Fuchs and A. Ellencweig, Recl. Trav. Chim. Pays-Bas, 1979, 98, 326.
8. Four methylene carbons of angularly nonsubstituted trans-TAD were equivalent and detected as a sole signal at δ: 46.53 ppm.
9. The high-field shift of the CSa-Me may be ascribed to steric reasons involving the effect of the lone-pair electrons of the nitrogen atom, in which facile conformation distortion can not occur by introduction of the N-methyl group.
10. -3. The reflection data were measured on a Rigaku RAXIS-RAPID Imaging Plate diffractometer with graphite monochromated Mo-Kα radiation (λ=0.7107 Å). The structures were solved by direct method. The hydrogens atoms were placed in calculated positions. The non-hydrogen atoms were refined anisotropically and the hydrogen atoms were not refined. The final cycle of full-matrix least-square refinement was based on 7216 observed reflections (I>-10.00σI) and 361 variable parameters and converged with unweighted (R) and weighted agreement factors (Rw) of 0.095 and 0.118, respectively [R1=0.049 for 3148 reflections with I>2.0σ (I)]. All calculations were performed using the teXsan crystallographic software Package of Molecular Structure Corporation (1985 & 1999).
11. The by-products contained 2a, 6a and other products; detailed data will be described in a succeeding paper.
12. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902: AMI calculations are performed using MOPAC (version 6.0), J. J. P. Stewart, QCPE program No. 455. The calculations were performed in the gas phase.
13. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902: AMI calculations are performed using MOPAC (version 6.0), J. J. P. Stewart, QCPE program No. 455. The calculations were performed in the gas phase.
14. The cis-adduct is predicted to be 5.50 kcal/mol more stable than the trans-adduct by ab initio calculation (HF/6-31G*//HF/6-31G*).