Synthesis of 1,3,6-Trisubstituted Azulenes Based on the 1-Acyloxyazulene Scaffold
An efficient synthetic route to 1,3,6‐trisubstituted azulenes based on the 1‐acyloxyazulene scaffold was developed. The 1‐position in azulene was substituted in the ring‐formation step with a functionalized acyloxy group. Additionally, the 3‐ and 6‐positions of azulene were functionalized with versa...
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| Veröffentlicht in: | European journal of organic chemistry 2016-11, Vol.2016 (33), p.5539-5544 |
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| container_end_page | 5544 |
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| container_issue | 33 |
| container_start_page | 5539 |
| container_title | European journal of organic chemistry |
| container_volume | 2016 |
| creator | Leino, Teppo O. Johansson, Niklas G. Devisscher, Lars Sipari, Nina Yli-Kauhaluoma, Jari Wallén, Erik A. A. |
| description | An efficient synthetic route to 1,3,6‐trisubstituted azulenes based on the 1‐acyloxyazulene scaffold was developed. The 1‐position in azulene was substituted in the ring‐formation step with a functionalized acyloxy group. Additionally, the 3‐ and 6‐positions of azulene were functionalized with versatile synthetic handles, a halogen atom and a formyl group.
We describe an efficient approach to the synthesis of 1,3,6‐trisubstituted azulenes based on the 1‐acyloxyazulene scaffold, in which the 3‐ and 6‐positions of the azulene were functionalized with versatile synthetic handles. |
| doi_str_mv | 10.1002/ejoc.201600962 |
| format | Article |
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We describe an efficient approach to the synthesis of 1,3,6‐trisubstituted azulenes based on the 1‐acyloxyazulene scaffold, in which the 3‐ and 6‐positions of the azulene were functionalized with versatile synthetic handles.</description><subject>Aromatic substitution</subject><subject>Azulenes</subject><subject>Carbocycles</subject><subject>Cross-coupling</subject><subject>Cyclization</subject><subject>Synthesis design</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EEqWwMkdirYsdO048lgrKR2mFWiibZTuOSAlxsRPR8OtJFVSxMd2d7nnupBeAc4yGGKHw0qytHoYIM4Q4Cw9ADyPOIWIcHbY9JRRiTl6PwYn3a7RjGO6Bp0VTVm_G5z6wWYAHZMDg0uW-Vr7Kq7oyaTD6rgtTGh9cSd-OtgxaIcBwpJvCbhvZrYOFlllmi_QUHGWy8Obst_bB8831cnwLp_PJ3Xg0hTpiOIQkDbEhmioUKcY1TZhOOM8SmkhDDIoIpyhODWNhzBIZKSVVRLUizKRKR0aSPrjo7m6c_ayNr8Ta1q5sXwqcUJrQmOO4pYYdpZ313plMbFz-IV0jMBK72MQuNrGPrRV4J3zlhWn-ocX1_Xz814Wdm_vKbPeudO-CxSSOxGo2EezxZTUjD7Hg5AfIDH_i</recordid><startdate>201611</startdate><enddate>201611</enddate><creator>Leino, Teppo O.</creator><creator>Johansson, Niklas G.</creator><creator>Devisscher, Lars</creator><creator>Sipari, Nina</creator><creator>Yli-Kauhaluoma, Jari</creator><creator>Wallén, Erik A. A.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2582-7971</orcidid><orcidid>https://orcid.org/0000-0002-2269-5179</orcidid><orcidid>https://orcid.org/0000-0003-0370-7653</orcidid><orcidid>https://orcid.org/0000-0002-8226-4813</orcidid></search><sort><creationdate>201611</creationdate><title>Synthesis of 1,3,6-Trisubstituted Azulenes Based on the 1-Acyloxyazulene Scaffold</title><author>Leino, Teppo O. ; Johansson, Niklas G. ; Devisscher, Lars ; Sipari, Nina ; Yli-Kauhaluoma, Jari ; Wallén, Erik A. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5612-3d21e3c4b05b69c486c899f848ae3e0539407de662768a5bbab54cb36edbc5ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Aromatic substitution</topic><topic>Azulenes</topic><topic>Carbocycles</topic><topic>Cross-coupling</topic><topic>Cyclization</topic><topic>Synthesis design</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leino, Teppo O.</creatorcontrib><creatorcontrib>Johansson, Niklas G.</creatorcontrib><creatorcontrib>Devisscher, Lars</creatorcontrib><creatorcontrib>Sipari, Nina</creatorcontrib><creatorcontrib>Yli-Kauhaluoma, Jari</creatorcontrib><creatorcontrib>Wallén, Erik A. A.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Leino, Teppo O.</au><au>Johansson, Niklas G.</au><au>Devisscher, Lars</au><au>Sipari, Nina</au><au>Yli-Kauhaluoma, Jari</au><au>Wallén, Erik A. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 1,3,6-Trisubstituted Azulenes Based on the 1-Acyloxyazulene Scaffold</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2016-11</date><risdate>2016</risdate><volume>2016</volume><issue>33</issue><spage>5539</spage><epage>5544</epage><pages>5539-5544</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient synthetic route to 1,3,6‐trisubstituted azulenes based on the 1‐acyloxyazulene scaffold was developed. The 1‐position in azulene was substituted in the ring‐formation step with a functionalized acyloxy group. Additionally, the 3‐ and 6‐positions of azulene were functionalized with versatile synthetic handles, a halogen atom and a formyl group.
We describe an efficient approach to the synthesis of 1,3,6‐trisubstituted azulenes based on the 1‐acyloxyazulene scaffold, in which the 3‐ and 6‐positions of the azulene were functionalized with versatile synthetic handles.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ejoc.201600962</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-2582-7971</orcidid><orcidid>https://orcid.org/0000-0002-2269-5179</orcidid><orcidid>https://orcid.org/0000-0003-0370-7653</orcidid><orcidid>https://orcid.org/0000-0002-8226-4813</orcidid></addata></record> |
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| ispartof | European journal of organic chemistry, 2016-11, Vol.2016 (33), p.5539-5544 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Aromatic substitution Azulenes Carbocycles Cross-coupling Cyclization Synthesis design |
| title | Synthesis of 1,3,6-Trisubstituted Azulenes Based on the 1-Acyloxyazulene Scaffold |
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