Structure of a cyclopenta[hi]indolizine

Kakehi, A.; Kitajima, Kunio; Itô, Shinya; Takusagawa, Nobuo

doi:10.1107/s0108270191014531

Cited by 2 publications

(3 citation statements)

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“…The bond distances and angles for the indolizine skeleton in the title compound are closer to those of 1-acetoxy-2,3-diphenylindolizine (Wadsworth, Bender, Smith, Luss & Weidner, 1986) and ethyl 1-trifluoromethylindolizine-3-carboxylate (Pritchard, 1988), than to those of ethyl 3,4-dihydrocyclopenta[hOindolizine-1-carboxylate (Kakehi, Kitajima, Ito & Takusagawa, 1992); this is because, in contrast to the annelation of a five-membered ring at the 1 and 8 positions of an indolizine ring, the less-hindered pyrone ring attached to the 2 and 3 positions does not cause a large distortion of the skeleton. On the other hand, the distances and angles for the 2-pyrone ring are similar to those found in various 2-pyrone derivatives (Thailambal & Vasantha Pattabhi, 1987;Thailambal, Vasantha Pattabhi & Gabe, 1986), except for the shortened C3--C4 and lengthened C4---C11 bonds.…”

Section: Commentmentioning

confidence: 99%

Structure of a pyrano[2,3-b]indolizine

Kakehi¹,

Kitajima²,

Ito³

et al. 1993

Acta Crystallogr C

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The pyrrole and pyridine rings in the indolizine skeleton of 3-acetyl-6-methyl-2H-pyrano [2,3-b]indolizin-2-one are planar [mean deviations 0.003 (2) and 0.003 (2)A, respectively] and inclined at 0.5 (2) ° to one another. The planar [mean deviation 0.004 (2) A] 2-pyrone ring, fused at the 2 and 3 positions of the indolizine ring, is also coplanar with the indolizine ring [dihedral angle 1.1 (2)°]. The delocalized ring system extends to the fused pyrone ring as indicated by the shortened C4--C3 bond of 1.375 (3)A. The acetyl group at the3 position is also coplanar with the pyrone ring [dihedral angle 0.5 (2)°].

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Section: Commentmentioning

confidence: 99%

Structure of a pyrano[2,3-b]indolizine

Kakehi¹,

Kitajima²,

Ito³

et al. 1993

Acta Crystallogr C

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“…This distortion must be caused by the annelation at the 1-and 8-positions in the indolizine skeleton, as in ethyl 3,4-dihydrocyclopenta[ht]indolizine-l-carboxylate (Kakehi, Kitajima, Ito & Takusagawa, 1992a) in which there is a five-membered ring at the 1-and 8-positions of the indolizine ring. On the other hand, the furan ring attached to the 2-and 3-positions as well as the benzoyl group does not cause a large distortion of the indolizine skeleton.…”

Section: Commentmentioning

confidence: 99%

“…The bond distances and angles in the indolizine skeletons of (2a) and (2b) are similar to those in 1-acetoxy-2,3-diphenylindolizine (Wadsworth, Bender, Smith, Luss & Weidner, 1986), ethyl 1-trifluoromethylindolizine-3-carboxylate (Pritchard, 1988), ethyl 3,7-dimethyl-2-(p-methylbenzoyl)thieno [2,3-b]indolizine-9-carboxylate (Kakehi, Ito, Sakurai & Urushido, 1991), and 3-acetyl-6-methyl-2H-pyrano[2,3-b]indolizin-2-one (Kakehi, Kitajima, Ito & Takusagawa, 1992b). Those in (2b) are also similar to those in (2a) except for the shortened C8--N1 bond (1.402A) and enlarged N1--C8--C7 and N1--C8--C9 bond angles [119.6 (2) and 111.8 (2) °, respectively].…”

Section: Commentmentioning

confidence: 99%