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Okano T, Sakaida T, Eguchi S. Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones. J Org Chem. 1996;61(25):8826-8830doi: 10.1021/jo961030g.
Okano, T., Sakaida, T., & Eguchi, S. (1996). Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones. The Journal of organic chemistry, 61(25), 8826-8830. https://doi.org/10.1021/jo961030g
Okano, Takashi, et al. "Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones." The Journal of organic chemistry vol. 61,25 (1996): 8826-8830. doi: https://doi.org/10.1021/jo961030g
Okano T, Sakaida T, Eguchi S. Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones. J Org Chem. 1996 Dec 13;61(25):8826-8830. doi: 10.1021/jo961030g. PMID: 11667861.
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J Org Chem. 1996 Dec 13;61(25):8826-8830. doi: 10.1021/jo961030g.

Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones.

The Journal of organic chemistry

Takashi Okano, Tsutomu Sakaida, Shoji Eguchi

Affiliations

  1. Department of Molecular Design and Engineering, Graduate School of Engineering,(dagger) Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-01, Japan.

PMID: 11667861 DOI: 10.1021/jo961030g

Abstract

Staudinger/aza-Wittig reaction of 6,6,6-trifluoro-5-oxohexanoyl azide with PPh(3) or PBu(3) was examined. A reactive intermediate acyl imine 1 was trapped by methanol. Without nucleophile, isomerized enamide form 3 was obtained. N-Iodobenzoylation and N-haloalkylation of 3 and following radical cyclization via the 5-exo or 6-exo mode gave benzoindolizidinone, indolizidinone, and quinolizidinone derivatives 10-14, which have a trifluoromethyl group at the bridgehead position adjacent to nitrogen. Although LiAlH(4) reduction of 10 and 11 gave a mixture of saturated benzoindolizidine 15 and amino alcohol 16, reduction with BH(3)/THF selectively gave the desired 15 and indolizidine 17 from 13.

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