First synthesis and cycloaddition reactions of 1-azaazulene N-ylide

Heterocycles

Volumn 59, Issue 1, 2003, Pages 63-66

  Fujii, Hiroyuki ^a   Iwafuji, Kaoru ^a   Sawae, Yoshiyuki ^a   Abe, Noritaka ^a   Kakehi, Akikazu ^b  

^a YAMAGUCHI UNIVERSITY   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 AZAAZULENE N YLIDE; 3A AZACYCLOPENT[A]AZULENE DERIVATIVE; AZULENE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CRYSTAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037224157     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-S15     Document Type: Article

References (11)

1. A. W. Johnson, 'Ylid Chemistry,' Academic Press, New York, 1966, chapter 7.
2. I. Zugravescu and M. Petrovanu, 'N-Ylid Chemistry,' McGraw-Hill, New York, 1976.
3. O. Tsuge and S. Kanemasa, Adv. Heterocycl. Chem., 1989, 45, 231.
4. A. Padwa, '1,3-Dipolar Cycloaddition Chemistry, Vols. 1 and 2,' Wiley, New York, 1984.
5. R. Huisgen, Angew. Chem., Int. Ed. Engl., 1963, 2, 565.
6. N. Abe, K. Odagiri, and A. Kahehi, J. Chem. Soc., Perkin Trans. 1, 1997, 2189.
7. Recent reviews see, N. Abe, Recent Res. Devel. Org. & Bioorg. Chem., 2001, 4, 17; N. Abe, Trends in Heterocycl. Chem., 2001, 7, 25.
8. Recent reviews see, N. Abe, Recent Res. Devel. Org. & Bioorg. Chem., 2001, 4, 17; N. Abe, Trends in Heterocycl. Chem., 2001, 7, 25.
9. N. Abe, Y. Fukumoto, H. Fujii, and A. Kakehi, Heterocycles, 2002, 5 6, 171.
10. +, 100), 286 (39), 271 (30), 200 (30).
11. 3, crystal dimension 0. 12 × 0.56 × 0.68 mm. Data were measured on a Rigaku AFC 5S radiation diffractmeter with graphite-monochromated Mo-Kα radiation. Total 3659 reflections (3530 unique) were collected using ω-2θ scan technique with in a 2θ range of 55.0°. The structure was solved by direct methods (SIR88), and refined a full-matrix least squares methods using 199 variables refined with 1658 reflections [I>2σ]. The final refinement converged to R = 0.060 and Rw = 0.063; selective bond lengths (Å): N(1) - C(1) 1.367(6), C(1) - C(2) 1.371(6), C(2) - C(3) 1.407(7), C(3) - C(4) 1.381(6), C(4) - C(5) 1.449(7), C(5) - C(6) 1.398(7), C(6) - C(7) 1.372(8), C(7) - C(8) 1.390(9), C(8) - C(9) 1.375(9), C(9) - C(10) 1.395(8), C(10) - C(11) 1.441(7), C(11) - C(12) 1.314(7), C(12) - N(1) 1.408(6).