Synthesis of Heteroannulated Indolopyrazines through Domino N–H Palladium-Catalyzed/Metal-Free Oxidative C–H Bond Activation

A convenient approach to [1,2,5]­oxadiazolo­[3′,4′:5,6]­pyrazino­[2,3-b]­indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald–Hartwig and subsequent annulation by intramolecular oxi...

Full description

Saved in:
Bibliographic Details
Published in:ACS omega 2020-06, Vol.5 (25), p.15681-15690
Main Authors: Kvashnin, Yuriy A, Verbitskiy, Egor V, Zhilina, Ekaterina F, Rusinov, Gennady L, Chupakhin, Oleg N, Charushin, Valery N
Format: Article
Language:English
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-a476t-4f5b3acbbdffac3d68e955eb5d6ad32fd86aabd371216380c4f3970d3607367e3
cites cdi_FETCH-LOGICAL-a476t-4f5b3acbbdffac3d68e955eb5d6ad32fd86aabd371216380c4f3970d3607367e3
container_end_page 15690
container_issue 25
container_start_page 15681
container_title ACS omega
container_volume 5
creator Kvashnin, Yuriy A
Verbitskiy, Egor V
Zhilina, Ekaterina F
Rusinov, Gennady L
Chupakhin, Oleg N
Charushin, Valery N
description A convenient approach to [1,2,5]­oxadiazolo­[3′,4′:5,6]­pyrazino­[2,3-b]­indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald–Hartwig and subsequent annulation by intramolecular oxidative cyclodehydrogenation. The photophysical properties for new polycycles have been measured.
doi_str_mv 10.1021/acsomega.0c01945
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_1dcc78611dcf41f5a9ea4694a34be87c</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_1dcc78611dcf41f5a9ea4694a34be87c</doaj_id><sourcerecordid>2421463844</sourcerecordid><originalsourceid>FETCH-LOGICAL-a476t-4f5b3acbbdffac3d68e955eb5d6ad32fd86aabd371216380c4f3970d3607367e3</originalsourceid><addsrcrecordid>eNp1ksFu1DAQhiMEolXpnaOPHEhrx46dvSCVLWVXKhQJOFsTe7LrVWIvdlKxPfUdeEOeBNNdED1wmtE__3yWR39RvGT0jNGKnYNJYcAVnFFD2UzUT4rjSihaMi7403_6o-I0pQ2llMmmair5vDjileSqEfy4uP-88-Mak0skdGSBI8YA3k89jGjJ0tvQh-0uwp3zmMi4jmFarcllGJwP5OPP-x8L8gn6HqybhnIOI_S7O7TnHzB35VVEJDffnYXR3SKZP9jfBm_JhclKVoN_UTzroE94eqgnxderd1_mi_L65v1yfnFdglByLEVXtxxM29quA8OtbHBW19jWVoLlVWcbCdBarljFJG-oER2fKWq5pIpLhfykWO65NsBGb6MbIO50AKcfhBBXGuLoTI-aWWNUI1munWBdDTMEIWcCuGixUSaz3uxZ26kd0Br0Y4T-EfTxxLu1XoVbrThnFa0z4NUBEMO3CdOoB5cM5jt6DFPSlaiYyN8QIlvp3mpiSCli9_cZRvXvHOg_OdCHHOSV1_uVPNGbMEWfD_t_-y8KRLqS</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2421463844</pqid></control><display><type>article</type><title>Synthesis of Heteroannulated Indolopyrazines through Domino N–H Palladium-Catalyzed/Metal-Free Oxidative C–H Bond Activation</title><source>PubMed Central(OpenAccess)</source><source>American Chemical Society (ACS) Open Access</source><creator>Kvashnin, Yuriy A ; Verbitskiy, Egor V ; Zhilina, Ekaterina F ; Rusinov, Gennady L ; Chupakhin, Oleg N ; Charushin, Valery N</creator><creatorcontrib>Kvashnin, Yuriy A ; Verbitskiy, Egor V ; Zhilina, Ekaterina F ; Rusinov, Gennady L ; Chupakhin, Oleg N ; Charushin, Valery N</creatorcontrib><description>A convenient approach to [1,2,5]­oxadiazolo­[3′,4′:5,6]­pyrazino­[2,3-b]­indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald–Hartwig and subsequent annulation by intramolecular oxidative cyclodehydrogenation. The photophysical properties for new polycycles have been measured.</description><identifier>ISSN: 2470-1343</identifier><identifier>EISSN: 2470-1343</identifier><identifier>DOI: 10.1021/acsomega.0c01945</identifier><identifier>PMID: 32637843</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>ACS omega, 2020-06, Vol.5 (25), p.15681-15690</ispartof><rights>Copyright © 2020 American Chemical Society 2020 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a476t-4f5b3acbbdffac3d68e955eb5d6ad32fd86aabd371216380c4f3970d3607367e3</citedby><cites>FETCH-LOGICAL-a476t-4f5b3acbbdffac3d68e955eb5d6ad32fd86aabd371216380c4f3970d3607367e3</cites><orcidid>0000-0002-1672-2476 ; 0000-0002-9613-8738</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acsomega.0c01945$$EPDF$$P50$$Gacs$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acsomega.0c01945$$EHTML$$P50$$Gacs$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27080,27924,27925,53791,53793,56762,56812</link.rule.ids></links><search><creatorcontrib>Kvashnin, Yuriy A</creatorcontrib><creatorcontrib>Verbitskiy, Egor V</creatorcontrib><creatorcontrib>Zhilina, Ekaterina F</creatorcontrib><creatorcontrib>Rusinov, Gennady L</creatorcontrib><creatorcontrib>Chupakhin, Oleg N</creatorcontrib><creatorcontrib>Charushin, Valery N</creatorcontrib><title>Synthesis of Heteroannulated Indolopyrazines through Domino N–H Palladium-Catalyzed/Metal-Free Oxidative C–H Bond Activation</title><title>ACS omega</title><addtitle>ACS Omega</addtitle><description>A convenient approach to [1,2,5]­oxadiazolo­[3′,4′:5,6]­pyrazino­[2,3-b]­indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald–Hartwig and subsequent annulation by intramolecular oxidative cyclodehydrogenation. The photophysical properties for new polycycles have been measured.</description><issn>2470-1343</issn><issn>2470-1343</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>N~.</sourceid><sourceid>DOA</sourceid><recordid>eNp1ksFu1DAQhiMEolXpnaOPHEhrx46dvSCVLWVXKhQJOFsTe7LrVWIvdlKxPfUdeEOeBNNdED1wmtE__3yWR39RvGT0jNGKnYNJYcAVnFFD2UzUT4rjSihaMi7403_6o-I0pQ2llMmmair5vDjileSqEfy4uP-88-Mak0skdGSBI8YA3k89jGjJ0tvQh-0uwp3zmMi4jmFarcllGJwP5OPP-x8L8gn6HqybhnIOI_S7O7TnHzB35VVEJDffnYXR3SKZP9jfBm_JhclKVoN_UTzroE94eqgnxderd1_mi_L65v1yfnFdglByLEVXtxxM29quA8OtbHBW19jWVoLlVWcbCdBarljFJG-oER2fKWq5pIpLhfykWO65NsBGb6MbIO50AKcfhBBXGuLoTI-aWWNUI1munWBdDTMEIWcCuGixUSaz3uxZ26kd0Br0Y4T-EfTxxLu1XoVbrThnFa0z4NUBEMO3CdOoB5cM5jt6DFPSlaiYyN8QIlvp3mpiSCli9_cZRvXvHOg_OdCHHOSV1_uVPNGbMEWfD_t_-y8KRLqS</recordid><startdate>20200630</startdate><enddate>20200630</enddate><creator>Kvashnin, Yuriy A</creator><creator>Verbitskiy, Egor V</creator><creator>Zhilina, Ekaterina F</creator><creator>Rusinov, Gennady L</creator><creator>Chupakhin, Oleg N</creator><creator>Charushin, Valery N</creator><general>American Chemical Society</general><scope>N~.</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-1672-2476</orcidid><orcidid>https://orcid.org/0000-0002-9613-8738</orcidid></search><sort><creationdate>20200630</creationdate><title>Synthesis of Heteroannulated Indolopyrazines through Domino N–H Palladium-Catalyzed/Metal-Free Oxidative C–H Bond Activation</title><author>Kvashnin, Yuriy A ; Verbitskiy, Egor V ; Zhilina, Ekaterina F ; Rusinov, Gennady L ; Chupakhin, Oleg N ; Charushin, Valery N</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a476t-4f5b3acbbdffac3d68e955eb5d6ad32fd86aabd371216380c4f3970d3607367e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kvashnin, Yuriy A</creatorcontrib><creatorcontrib>Verbitskiy, Egor V</creatorcontrib><creatorcontrib>Zhilina, Ekaterina F</creatorcontrib><creatorcontrib>Rusinov, Gennady L</creatorcontrib><creatorcontrib>Chupakhin, Oleg N</creatorcontrib><creatorcontrib>Charushin, Valery N</creatorcontrib><collection>American Chemical Society (ACS) Open Access</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>ACS omega</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kvashnin, Yuriy A</au><au>Verbitskiy, Egor V</au><au>Zhilina, Ekaterina F</au><au>Rusinov, Gennady L</au><au>Chupakhin, Oleg N</au><au>Charushin, Valery N</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Heteroannulated Indolopyrazines through Domino N–H Palladium-Catalyzed/Metal-Free Oxidative C–H Bond Activation</atitle><jtitle>ACS omega</jtitle><addtitle>ACS Omega</addtitle><date>2020-06-30</date><risdate>2020</risdate><volume>5</volume><issue>25</issue><spage>15681</spage><epage>15690</epage><pages>15681-15690</pages><issn>2470-1343</issn><eissn>2470-1343</eissn><abstract>A convenient approach to [1,2,5]­oxadiazolo­[3′,4′:5,6]­pyrazino­[2,3-b]­indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald–Hartwig and subsequent annulation by intramolecular oxidative cyclodehydrogenation. The photophysical properties for new polycycles have been measured.</abstract><pub>American Chemical Society</pub><pmid>32637843</pmid><doi>10.1021/acsomega.0c01945</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-1672-2476</orcidid><orcidid>https://orcid.org/0000-0002-9613-8738</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2470-1343
ispartof ACS omega, 2020-06, Vol.5 (25), p.15681-15690
issn 2470-1343
2470-1343
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_1dcc78611dcf41f5a9ea4694a34be87c
source PubMed Central(OpenAccess); American Chemical Society (ACS) Open Access
title Synthesis of Heteroannulated Indolopyrazines through Domino N–H Palladium-Catalyzed/Metal-Free Oxidative C–H Bond Activation
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T09%3A37%3A15IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Heteroannulated%20Indolopyrazines%20through%20Domino%20N%E2%80%93H%20Palladium-Catalyzed/Metal-Free%20Oxidative%20C%E2%80%93H%20Bond%20Activation&rft.jtitle=ACS%20omega&rft.au=Kvashnin,%20Yuriy%20A&rft.date=2020-06-30&rft.volume=5&rft.issue=25&rft.spage=15681&rft.epage=15690&rft.pages=15681-15690&rft.issn=2470-1343&rft.eissn=2470-1343&rft_id=info:doi/10.1021/acsomega.0c01945&rft_dat=%3Cproquest_doaj_%3E2421463844%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a476t-4f5b3acbbdffac3d68e955eb5d6ad32fd86aabd371216380c4f3970d3607367e3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2421463844&rft_id=info:pmid/32637843&rfr_iscdi=true