Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles
Versatile procedures for fluorocyclization of various kinds of tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo(furo)[2.3-b]indoles were developed. •Versatile procedures for fluorocyclization of tryptamine and tryptophol derivatives were developed.•Various kinds of...
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| Veröffentlicht in: | Journal of fluorine chemistry 2014-09, Vol.165, p.7-13 |
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| creator | Fujiwara, Tomoya Seki, Takayuki Yakura, Takayuki Takeuchi, Yoshio |
| description | Versatile procedures for fluorocyclization of various kinds of tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo(furo)[2.3-b]indoles were developed.
•Versatile procedures for fluorocyclization of tryptamine and tryptophol derivatives were developed.•Various kinds of 3a-fluoropyrrolo(furo)[2.3-b]indoles were obtained successfully according to our procedures.•N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ is effective for fluorocyclization.•Electron-withdrawing groups at the indole nitrogen or 5-position lowers reactivity of fluorocyclization.•Use of NaHCO3 as an acid trap can improve the yields of acid-labile 3a-fluoropyrrolo(furo)[2.3-b]indoles.
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. |
| doi_str_mv | 10.1016/j.jfluchem.2014.05.011 |
| format | Article |
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•Versatile procedures for fluorocyclization of tryptamine and tryptophol derivatives were developed.•Various kinds of 3a-fluoropyrrolo(furo)[2.3-b]indoles were obtained successfully according to our procedures.•N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ is effective for fluorocyclization.•Electron-withdrawing groups at the indole nitrogen or 5-position lowers reactivity of fluorocyclization.•Use of NaHCO3 as an acid trap can improve the yields of acid-labile 3a-fluoropyrrolo(furo)[2.3-b]indoles.
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.</description><identifier>ISSN: 0022-1139</identifier><identifier>EISSN: 1873-3328</identifier><identifier>DOI: 10.1016/j.jfluchem.2014.05.011</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>Bearing ; Derivatives ; Fluorination ; Fluorine ; Fluorocyclization ; Furo[2,3-b]indole ; Indoles ; Pyrrolo[2,3-b]indole ; Synthesis ; Tryptamine ; Tryptamines ; Tryptophol</subject><ispartof>Journal of fluorine chemistry, 2014-09, Vol.165, p.7-13</ispartof><rights>2014 Elsevier B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c411t-42b1283a4796d867cfdc47f3292d24173391e2916ca5b52a9dc6cbe562c292e93</citedby><cites>FETCH-LOGICAL-c411t-42b1283a4796d867cfdc47f3292d24173391e2916ca5b52a9dc6cbe562c292e93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.jfluchem.2014.05.011$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Fujiwara, Tomoya</creatorcontrib><creatorcontrib>Seki, Takayuki</creatorcontrib><creatorcontrib>Yakura, Takayuki</creatorcontrib><creatorcontrib>Takeuchi, Yoshio</creatorcontrib><title>Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles</title><title>Journal of fluorine chemistry</title><description>Versatile procedures for fluorocyclization of various kinds of tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo(furo)[2.3-b]indoles were developed.
•Versatile procedures for fluorocyclization of tryptamine and tryptophol derivatives were developed.•Various kinds of 3a-fluoropyrrolo(furo)[2.3-b]indoles were obtained successfully according to our procedures.•N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ is effective for fluorocyclization.•Electron-withdrawing groups at the indole nitrogen or 5-position lowers reactivity of fluorocyclization.•Use of NaHCO3 as an acid trap can improve the yields of acid-labile 3a-fluoropyrrolo(furo)[2.3-b]indoles.
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.</description><subject>Bearing</subject><subject>Derivatives</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Fluorocyclization</subject><subject>Furo[2,3-b]indole</subject><subject>Indoles</subject><subject>Pyrrolo[2,3-b]indole</subject><subject>Synthesis</subject><subject>Tryptamine</subject><subject>Tryptamines</subject><subject>Tryptophol</subject><issn>0022-1139</issn><issn>1873-3328</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkc9q3DAQxkVpoNtNX6H42EPtaCT53y0hNE1goZfkFILQSiOiRWs5kr2wfYw8cbW4yaGXnoaZ-X0fzHyEfAVaAYXmYlftrJ_1M-4rRkFUtK4owAeygq7lJees-0hWlDJWAvD-E_mc0o5S2tK2W5HXh4R29sUYg0YzR0yFDbHIhiFPjtq732pyYSiCLaZ4HCe1dwMWajBLG8bn4AuD0R0yd8jyKRRclYvBeIwx-PDIvvNy--QGE3wmTuJ3xM7xn_05ObPKJ_zyt67Jw82P--vbcvPr59311abUAmAqBdsC67gSbd-Yrmm1NVq0lrOeGSag5bwHZD00WtXbmqne6EZvsW6Yzgj2fE2-Lb759pcZ0yT3Lmn0Xg0Y5iShFaLpmWAntFlQHUNKEa0co9ureJRA5SkEuZNvIchTCJLWMoeQhZeLEPMhB4dRJu1wyK92EfUkTXD_s_gD6O2XCg</recordid><startdate>20140901</startdate><enddate>20140901</enddate><creator>Fujiwara, Tomoya</creator><creator>Seki, Takayuki</creator><creator>Yakura, Takayuki</creator><creator>Takeuchi, Yoshio</creator><general>Elsevier B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20140901</creationdate><title>Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles</title><author>Fujiwara, Tomoya ; Seki, Takayuki ; Yakura, Takayuki ; Takeuchi, Yoshio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c411t-42b1283a4796d867cfdc47f3292d24173391e2916ca5b52a9dc6cbe562c292e93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Bearing</topic><topic>Derivatives</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Fluorocyclization</topic><topic>Furo[2,3-b]indole</topic><topic>Indoles</topic><topic>Pyrrolo[2,3-b]indole</topic><topic>Synthesis</topic><topic>Tryptamine</topic><topic>Tryptamines</topic><topic>Tryptophol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fujiwara, Tomoya</creatorcontrib><creatorcontrib>Seki, Takayuki</creatorcontrib><creatorcontrib>Yakura, Takayuki</creatorcontrib><creatorcontrib>Takeuchi, Yoshio</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of fluorine chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fujiwara, Tomoya</au><au>Seki, Takayuki</au><au>Yakura, Takayuki</au><au>Takeuchi, Yoshio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles</atitle><jtitle>Journal of fluorine chemistry</jtitle><date>2014-09-01</date><risdate>2014</risdate><volume>165</volume><spage>7</spage><epage>13</epage><pages>7-13</pages><issn>0022-1139</issn><eissn>1873-3328</eissn><abstract>Versatile procedures for fluorocyclization of various kinds of tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo(furo)[2.3-b]indoles were developed.
•Versatile procedures for fluorocyclization of tryptamine and tryptophol derivatives were developed.•Various kinds of 3a-fluoropyrrolo(furo)[2.3-b]indoles were obtained successfully according to our procedures.•N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ is effective for fluorocyclization.•Electron-withdrawing groups at the indole nitrogen or 5-position lowers reactivity of fluorocyclization.•Use of NaHCO3 as an acid trap can improve the yields of acid-labile 3a-fluoropyrrolo(furo)[2.3-b]indoles.
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.</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.jfluchem.2014.05.011</doi><tpages>7</tpages></addata></record> |
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| subjects | Bearing Derivatives Fluorination Fluorine Fluorocyclization Furo[2,3-b]indole Indoles Pyrrolo[2,3-b]indole Synthesis Tryptamine Tryptamines Tryptophol |
| title | Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles |
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