One-pot synthesis of disulfide-linked N-sulfonylazetidin-2-imines via a copper-catalyzed multicomponent cascade reaction
A copper-catalyzed, three-component reaction between a sulfonyl azide, an alkyne, and a 2-aminothiophenol derived Schiff base is reported. This novel one-pot procedure involves a click reaction, a formal [2+2] cycloaddition, and S–S coupling, therefore, providing a unique method for the synthesis of...
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Veröffentlicht in: | Tetrahedron 2013-11, Vol.69 (47), p.10134-10138 |
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creator | Shang, Yongjia Liao, Kaisheng He, Xinwei Hu, Jinsong |
description | A copper-catalyzed, three-component reaction between a sulfonyl azide, an alkyne, and a 2-aminothiophenol derived Schiff base is reported. This novel one-pot procedure involves a click reaction, a formal [2+2] cycloaddition, and S–S coupling, therefore, providing a unique method for the synthesis of novel disulfide-linked N-sulfonylazetidin-2-imines under mild conditions.
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doi_str_mv | 10.1016/j.tet.2013.09.033 |
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[Display omitted]</description><subject>Alkynes</subject><subject>Cascade chemical reactions</subject><subject>Coupling reaction</subject><subject>Cycloaddition</subject><subject>Joining</subject><subject>Ketenimines</subject><subject>Multicomponent reaction</subject><subject>N-Sulfonylazetidinimines</subject><subject>Schiff bases</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kE1v1DAURS0EUofSH9Cdl2wcnj_iScQKVVCQKrqBteU4L-obEjvYnorpryejYc3qSk_3POkexm4lNBKk_XBoKtZGgdQN9A1o_YrtpLFGtEba12wHYEAYUHDF3pZyAAApld6xP48RxZoqL6dYn7BQ4WniI5XjPNGIYqb4C0f-XZwPKZ5m_4KVRopCCVooYuHP5LnnIa0rZhF89fPpZUOW41wppGVNEWPlwZfgR-QZfaiU4jv2ZvJzwZt_ec1-fvn84-6reHi8_3b36UEEraGKrkVr-l4NU8BWWRw6D0a2Vhk_jVpLvTfY-aE31upW-kH2g1Ua9l3bt1OnWn3N3l_-rjn9PmKpbqEScJ59xHQsTu6NsZ1S_bkqL9WQUykZJ7dmWnw-OQnubNkd3GbZnS076N1meWM-XhjcNjwTZlcCYQw4UsZQ3ZjoP_Rf8qiGnQ</recordid><startdate>20131125</startdate><enddate>20131125</enddate><creator>Shang, Yongjia</creator><creator>Liao, Kaisheng</creator><creator>He, Xinwei</creator><creator>Hu, Jinsong</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20131125</creationdate><title>One-pot synthesis of disulfide-linked N-sulfonylazetidin-2-imines via a copper-catalyzed multicomponent cascade reaction</title><author>Shang, Yongjia ; Liao, Kaisheng ; He, Xinwei ; Hu, Jinsong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-85e64992bfce526eb8a0415624afd331374e8ab9466351ab19b623078595f8253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkynes</topic><topic>Cascade chemical reactions</topic><topic>Coupling reaction</topic><topic>Cycloaddition</topic><topic>Joining</topic><topic>Ketenimines</topic><topic>Multicomponent reaction</topic><topic>N-Sulfonylazetidinimines</topic><topic>Schiff bases</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shang, Yongjia</creatorcontrib><creatorcontrib>Liao, Kaisheng</creatorcontrib><creatorcontrib>He, Xinwei</creatorcontrib><creatorcontrib>Hu, Jinsong</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shang, Yongjia</au><au>Liao, Kaisheng</au><au>He, Xinwei</au><au>Hu, Jinsong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-pot synthesis of disulfide-linked N-sulfonylazetidin-2-imines via a copper-catalyzed multicomponent cascade reaction</atitle><jtitle>Tetrahedron</jtitle><date>2013-11-25</date><risdate>2013</risdate><volume>69</volume><issue>47</issue><spage>10134</spage><epage>10138</epage><pages>10134-10138</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A copper-catalyzed, three-component reaction between a sulfonyl azide, an alkyne, and a 2-aminothiophenol derived Schiff base is reported. This novel one-pot procedure involves a click reaction, a formal [2+2] cycloaddition, and S–S coupling, therefore, providing a unique method for the synthesis of novel disulfide-linked N-sulfonylazetidin-2-imines under mild conditions.
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source | ScienceDirect Journals (5 years ago - present) |
subjects | Alkynes Cascade chemical reactions Coupling reaction Cycloaddition Joining Ketenimines Multicomponent reaction N-Sulfonylazetidinimines Schiff bases Synthesis Tetrahedrons |
title | One-pot synthesis of disulfide-linked N-sulfonylazetidin-2-imines via a copper-catalyzed multicomponent cascade reaction |
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