Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences

The unexpected reactions of indoline hemiaminals affords 2,5‐diaryl‐4‐hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild react...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2024-01, Vol.27 (4), p.n/a
Main Authors: Yamada, Koji, Tsubogo, Tetsu, Kanazawa, Hikaru, Ishizuka, Sayaka, Ohyama, Koutaro, Kaida, Masaki, Abe, Takumi
Format: Article
Language:English
Subjects:
hemiaminals
indoles
ring-switch
thiazolo[4.5-b]indoles
thioamides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c3330-3d69d3393260d23288abb3bffe55bac93286c00e76eeccf29e582a3e1d5d6a643
cites cdi_FETCH-LOGICAL-c3330-3d69d3393260d23288abb3bffe55bac93286c00e76eeccf29e582a3e1d5d6a643
container_end_page n/a
container_issue 4
container_start_page
container_title European journal of organic chemistry
container_volume 27
creator Yamada, Koji
Tsubogo, Tetsu
Kanazawa, Hikaru
Ishizuka, Sayaka
Ohyama, Koutaro
Kaida, Masaki
Abe, Takumi
description The unexpected reactions of indoline hemiaminals affords 2,5‐diaryl‐4‐hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance (17 examples, up to 99 % yield). Further transformations of the thiazolines provide a direct entry to dihydrothiazolo[4,5‐b]indoles and thiazolo[4,5‐b]indoles. Open and shut!!: Unprecedented modular synthesis of thiazolo[4.5‐b]indoles was accomplished by a unique ring switch/cyclization sequences of hemiaminals.
doi_str_mv 10.1002/ejoc.202301130
format article
fullrecord <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ejoc_202301130</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>EJOC202301130</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3330-3d69d3393260d23288abb3bffe55bac93286c00e76eeccf29e582a3e1d5d6a643</originalsourceid><addsrcrecordid>eNqFkM1Kw0AUhQdRsFa3rvMApr0zNxkzSwn1j0LBVBBEwmRyY6fEjGZaS7ryEXxGn8SWii5d3cPlfGfxMXbKYcABxJDmzgwECATOEfZYj4NSIUgF-5scYRRyhQ-H7Mj7OQAoKXmPZalrjPUUZF2zmJG3PnBVMJ1ZvXa1e4zO4q-Pz-LJNqWryQfvVgd3tnkOspVdmNkw7Uxt13phXRNk9LakxpA_ZgeVrj2d_Nw-u78cTdPrcDy5ukkvxqFBRAixlKpEVCgklAJFkuiiwKKqKI4LbTb_RBoAOpdExlRCUZwIjcTLuJRaRthng92uaZ33LVX5a2tfdNvlHPKtknyrJP9VsgHUDljZmrp_2vnodpL-sd-dUGdI</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences</title><source>Wiley-Blackwell Read &amp; Publish Collection</source><creator>Yamada, Koji ; Tsubogo, Tetsu ; Kanazawa, Hikaru ; Ishizuka, Sayaka ; Ohyama, Koutaro ; Kaida, Masaki ; Abe, Takumi</creator><creatorcontrib>Yamada, Koji ; Tsubogo, Tetsu ; Kanazawa, Hikaru ; Ishizuka, Sayaka ; Ohyama, Koutaro ; Kaida, Masaki ; Abe, Takumi</creatorcontrib><description>The unexpected reactions of indoline hemiaminals affords 2,5‐diaryl‐4‐hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance (17 examples, up to 99 % yield). Further transformations of the thiazolines provide a direct entry to dihydrothiazolo[4,5‐b]indoles and thiazolo[4,5‐b]indoles. Open and shut!!: Unprecedented modular synthesis of thiazolo[4.5‐b]indoles was accomplished by a unique ring switch/cyclization sequences of hemiaminals.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202301130</identifier><language>eng</language><subject>hemiaminals ; indoles ; ring-switch ; thiazolo[4.5-b]indoles ; thioamides</subject><ispartof>European journal of organic chemistry, 2024-01, Vol.27 (4), p.n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3330-3d69d3393260d23288abb3bffe55bac93286c00e76eeccf29e582a3e1d5d6a643</citedby><cites>FETCH-LOGICAL-c3330-3d69d3393260d23288abb3bffe55bac93286c00e76eeccf29e582a3e1d5d6a643</cites><orcidid>0000-0002-5084-7571 ; 0000-0003-1729-1097</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Yamada, Koji</creatorcontrib><creatorcontrib>Tsubogo, Tetsu</creatorcontrib><creatorcontrib>Kanazawa, Hikaru</creatorcontrib><creatorcontrib>Ishizuka, Sayaka</creatorcontrib><creatorcontrib>Ohyama, Koutaro</creatorcontrib><creatorcontrib>Kaida, Masaki</creatorcontrib><creatorcontrib>Abe, Takumi</creatorcontrib><title>Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences</title><title>European journal of organic chemistry</title><description>The unexpected reactions of indoline hemiaminals affords 2,5‐diaryl‐4‐hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance (17 examples, up to 99 % yield). Further transformations of the thiazolines provide a direct entry to dihydrothiazolo[4,5‐b]indoles and thiazolo[4,5‐b]indoles. Open and shut!!: Unprecedented modular synthesis of thiazolo[4.5‐b]indoles was accomplished by a unique ring switch/cyclization sequences of hemiaminals.</description><subject>hemiaminals</subject><subject>indoles</subject><subject>ring-switch</subject><subject>thiazolo[4.5-b]indoles</subject><subject>thioamides</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkM1Kw0AUhQdRsFa3rvMApr0zNxkzSwn1j0LBVBBEwmRyY6fEjGZaS7ryEXxGn8SWii5d3cPlfGfxMXbKYcABxJDmzgwECATOEfZYj4NSIUgF-5scYRRyhQ-H7Mj7OQAoKXmPZalrjPUUZF2zmJG3PnBVMJ1ZvXa1e4zO4q-Pz-LJNqWryQfvVgd3tnkOspVdmNkw7Uxt13phXRNk9LakxpA_ZgeVrj2d_Nw-u78cTdPrcDy5ukkvxqFBRAixlKpEVCgklAJFkuiiwKKqKI4LbTb_RBoAOpdExlRCUZwIjcTLuJRaRthng92uaZ33LVX5a2tfdNvlHPKtknyrJP9VsgHUDljZmrp_2vnodpL-sd-dUGdI</recordid><startdate>20240122</startdate><enddate>20240122</enddate><creator>Yamada, Koji</creator><creator>Tsubogo, Tetsu</creator><creator>Kanazawa, Hikaru</creator><creator>Ishizuka, Sayaka</creator><creator>Ohyama, Koutaro</creator><creator>Kaida, Masaki</creator><creator>Abe, Takumi</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-5084-7571</orcidid><orcidid>https://orcid.org/0000-0003-1729-1097</orcidid></search><sort><creationdate>20240122</creationdate><title>Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences</title><author>Yamada, Koji ; Tsubogo, Tetsu ; Kanazawa, Hikaru ; Ishizuka, Sayaka ; Ohyama, Koutaro ; Kaida, Masaki ; Abe, Takumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3330-3d69d3393260d23288abb3bffe55bac93286c00e76eeccf29e582a3e1d5d6a643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>hemiaminals</topic><topic>indoles</topic><topic>ring-switch</topic><topic>thiazolo[4.5-b]indoles</topic><topic>thioamides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamada, Koji</creatorcontrib><creatorcontrib>Tsubogo, Tetsu</creatorcontrib><creatorcontrib>Kanazawa, Hikaru</creatorcontrib><creatorcontrib>Ishizuka, Sayaka</creatorcontrib><creatorcontrib>Ohyama, Koutaro</creatorcontrib><creatorcontrib>Kaida, Masaki</creatorcontrib><creatorcontrib>Abe, Takumi</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamada, Koji</au><au>Tsubogo, Tetsu</au><au>Kanazawa, Hikaru</au><au>Ishizuka, Sayaka</au><au>Ohyama, Koutaro</au><au>Kaida, Masaki</au><au>Abe, Takumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences</atitle><jtitle>European journal of organic chemistry</jtitle><date>2024-01-22</date><risdate>2024</risdate><volume>27</volume><issue>4</issue><epage>n/a</epage><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The unexpected reactions of indoline hemiaminals affords 2,5‐diaryl‐4‐hydroxythiazolines through a thioamidation/ring switch sequence. The key to success of this transformation is to use a thioamide as a thiazoline precursor under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance (17 examples, up to 99 % yield). Further transformations of the thiazolines provide a direct entry to dihydrothiazolo[4,5‐b]indoles and thiazolo[4,5‐b]indoles. Open and shut!!: Unprecedented modular synthesis of thiazolo[4.5‐b]indoles was accomplished by a unique ring switch/cyclization sequences of hemiaminals.</abstract><doi>10.1002/ejoc.202301130</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-5084-7571</orcidid><orcidid>https://orcid.org/0000-0003-1729-1097</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1434-193X
ispartof European journal of organic chemistry, 2024-01, Vol.27 (4), p.n/a
issn 1434-193X
1099-0690
language eng
recordid cdi_crossref_primary_10_1002_ejoc_202301130
source Wiley-Blackwell Read & Publish Collection
subjects hemiaminals
indoles
ring-switch
thiazolo[4.5-b]indoles
thioamides
title Concise Synthesis of Thiazolo[4,5‐b]indoles via Ring Switch/Cyclization Sequences
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T12%3A43%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Concise%20Synthesis%20of%20Thiazolo%5B4,5%E2%80%90b%5Dindoles%20via%20Ring%20Switch/Cyclization%20Sequences&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Yamada,%20Koji&rft.date=2024-01-22&rft.volume=27&rft.issue=4&rft.epage=n/a&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.202301130&rft_dat=%3Cwiley_cross%3EEJOC202301130%3C/wiley_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3330-3d69d3393260d23288abb3bffe55bac93286c00e76eeccf29e582a3e1d5d6a643%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true