Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles

Tomoya Fujiwara; Takayuki Seki; Takayuki Yakura; Yoshio Takeuchi

doi:10.1016/j.jfluchem.2014.05.011

Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles

Tomoya Fujiwara^*, Takayuki Seki, Takayuki Yakura, Yoshio Takeuchi

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

25 被引用数 (Scopus)

抄録

Versatile procedures for fluorocyclization of various tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo[2.3-b] indoles and 3a-fluorofuro[2.3-b]indoles, respectively were developed employing N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ as the electrophilic fluorinating agent. The use of NaHCO₃ for fluorocyclization was effective in improving the yield of acid-labile fluoropyrrolo(furo)indoles. Our procedures are especially useful for the synthesis of fluoropyrrolo(furo)indoles bearing a free NH indole group.

本文言語	英語
ページ（範囲）	7-13
ページ数	7
ジャーナル	Journal of Fluorine Chemistry
巻	165
DOI	https://doi.org/10.1016/j.jfluchem.2014.05.011
出版ステータス	出版済み - 2014/09

ASJC Scopus 主題領域

生化学
環境化学
物理化学および理論化学
有機化学
無機化学

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10.1016/j.jfluchem.2014.05.011

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引用スタイル

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title = "Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles",

abstract = "Versatile procedures for fluorocyclization of various tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo[2.3-b] indoles and 3a-fluorofuro[2.3-b]indoles, respectively were developed employing N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor{\texttrademark} as the electrophilic fluorinating agent. The use of NaHCO3 for fluorocyclization was effective in improving the yield of acid-labile fluoropyrrolo(furo)indoles. Our procedures are especially useful for the synthesis of fluoropyrrolo(furo)indoles bearing a free NH indole group.",

keywords = "Fluorocyclization, Furo[2,3-b]indole, Pyrrolo[2,3-b]indole, Tryptamine, Tryptophol",

author = "Tomoya Fujiwara and Takayuki Seki and Takayuki Yakura and Yoshio Takeuchi",

year = "2014",

month = sep,

doi = "10.1016/j.jfluchem.2014.05.011",

language = "英語",

volume = "165",

pages = "7--13",

journal = "Journal of Fluorine Chemistry",

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T1 - Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles

AU - Fujiwara, Tomoya

AU - Seki, Takayuki

AU - Yakura, Takayuki

AU - Takeuchi, Yoshio

PY - 2014/9

Y1 - 2014/9

N2 - Versatile procedures for fluorocyclization of various tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo[2.3-b] indoles and 3a-fluorofuro[2.3-b]indoles, respectively were developed employing N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ as the electrophilic fluorinating agent. The use of NaHCO3 for fluorocyclization was effective in improving the yield of acid-labile fluoropyrrolo(furo)indoles. Our procedures are especially useful for the synthesis of fluoropyrrolo(furo)indoles bearing a free NH indole group.

AB - Versatile procedures for fluorocyclization of various tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo[2.3-b] indoles and 3a-fluorofuro[2.3-b]indoles, respectively were developed employing N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ as the electrophilic fluorinating agent. The use of NaHCO3 for fluorocyclization was effective in improving the yield of acid-labile fluoropyrrolo(furo)indoles. Our procedures are especially useful for the synthesis of fluoropyrrolo(furo)indoles bearing a free NH indole group.

KW - Fluorocyclization

KW - Furo[2,3-b]indole

KW - Pyrrolo[2,3-b]indole

KW - Tryptamine

KW - Tryptophol

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U2 - 10.1016/j.jfluchem.2014.05.011

DO - 10.1016/j.jfluchem.2014.05.011

M3 - 学術論文

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SN - 0022-1139

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SP - 7

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JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

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