Thermal and photochemical reactions of steroidal α-azido ketones
Photolysis of 9α-azido-3β,20β-diacetoxy-5α-pregnan-11-one in methanol gave the N-acyl imine 11-aza-3β,20β-diacetoxy-C-homo-5α-pregn-9,11-en-12-one 4 and the aminoketone 9a-aza-3β,20β-diacetoxy-9-methoxy-B-homo-5α-pregnan-11-one 7 . In dichloromethane containing triethylamine the irradiation of this...
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| Veröffentlicht in: | Canadian journal of chemistry 1992-09, Vol.70 (9), p.2405-2412 |
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| container_title | Canadian journal of chemistry |
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| creator | Edwards, O. E Douglas, J. L Horwell, D. C Rank, W Sano, T |
| description | Photolysis of 9α-azido-3β,20β-diacetoxy-5α-pregnan-11-one in methanol gave the N-acyl imine 11-aza-3β,20β-diacetoxy-C-homo-5α-pregn-9,11-en-12-one
4
and the aminoketone 9a-aza-3β,20β-diacetoxy-9-methoxy-B-homo-5α-pregnan-11-one
7
. In dichloromethane containing triethylamine the irradiation of this azide gave the N-acyl imine
4
and the α,β-unsaturated amino ketone 9a-aza-3β,20β-diacetoxy-B-homo-5α-pregn-8-en-11-one
8
. Thermolysis or photolysis of 12α-azido-3α,20β-diacetoxy-5β-pregnan-11-one gave the N-acyl imine 12-aza-3α,20β-diacetoxy-C-homo-5β-pregn-12-en-11-one
10
as major product. Photolysis of 20β-acetoxy-12α-azido-3α-hydroxy-5β-pregnan-11-one gave the 3-hydroxy analogue of
10
. Transformation products of the N-acyl imines are described. |
| doi_str_mv | 10.1139/v92-305 |
| format | Article |
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4
and the aminoketone 9a-aza-3β,20β-diacetoxy-9-methoxy-B-homo-5α-pregnan-11-one
7
. In dichloromethane containing triethylamine the irradiation of this azide gave the N-acyl imine
4
and the α,β-unsaturated amino ketone 9a-aza-3β,20β-diacetoxy-B-homo-5α-pregn-8-en-11-one
8
. Thermolysis or photolysis of 12α-azido-3α,20β-diacetoxy-5β-pregnan-11-one gave the N-acyl imine 12-aza-3α,20β-diacetoxy-C-homo-5β-pregn-12-en-11-one
10
as major product. Photolysis of 20β-acetoxy-12α-azido-3α-hydroxy-5β-pregnan-11-one gave the 3-hydroxy analogue of
10
. Transformation products of the N-acyl imines are described.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v92-305</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><ispartof>Canadian journal of chemistry, 1992-09, Vol.70 (9), p.2405-2412</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c322t-1e45b4abf6e6ee415b3d697a4f61a3e4ccece030438fdc7b1e113fdecad65c7f3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v92-305$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v92-305$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,780,784,2932,27924,27925,64428,65234</link.rule.ids></links><search><creatorcontrib>Edwards, O. E</creatorcontrib><creatorcontrib>Douglas, J. L</creatorcontrib><creatorcontrib>Horwell, D. C</creatorcontrib><creatorcontrib>Rank, W</creatorcontrib><creatorcontrib>Sano, T</creatorcontrib><title>Thermal and photochemical reactions of steroidal α-azido ketones</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>Photolysis of 9α-azido-3β,20β-diacetoxy-5α-pregnan-11-one in methanol gave the N-acyl imine 11-aza-3β,20β-diacetoxy-C-homo-5α-pregn-9,11-en-12-one
4
and the aminoketone 9a-aza-3β,20β-diacetoxy-9-methoxy-B-homo-5α-pregnan-11-one
7
. In dichloromethane containing triethylamine the irradiation of this azide gave the N-acyl imine
4
and the α,β-unsaturated amino ketone 9a-aza-3β,20β-diacetoxy-B-homo-5α-pregn-8-en-11-one
8
. Thermolysis or photolysis of 12α-azido-3α,20β-diacetoxy-5β-pregnan-11-one gave the N-acyl imine 12-aza-3α,20β-diacetoxy-C-homo-5β-pregn-12-en-11-one
10
as major product. Photolysis of 20β-acetoxy-12α-azido-3α-hydroxy-5β-pregnan-11-one gave the 3-hydroxy analogue of
10
. Transformation products of the N-acyl imines are described.</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><recordid>eNp1j81KAzEURoMoOFbxFWalIETzN3_LUqwKBTd1HTI3N8xoZ1KSQdC38kV8JlNaXAiuLvfjcOAQcsnZLeeyuXtvBJWsOCIZVzWjUjT8mGSMsZoqpsQpOYvxNb0VE0VG5usOw2A2uRltvu385KHDoYe0BDQw9X6MuXd5nDD43qb5-4uaz976_A0nP2I8JyfObCJeHO6MvCzv14tHunp-eFrMVxSkEBPlqIpWmdaVWCIqXrTSlk1llCu5kagAEJBJpmTtLFQtx1TjLIKxZQGVkzNyvfdC8DEGdHob-sGED82Z3pXrVK5TeSKv9uQYIGBEE6D7hQ-Q3tqd8uZ_8K_1B1BiaSk</recordid><startdate>19920901</startdate><enddate>19920901</enddate><creator>Edwards, O. E</creator><creator>Douglas, J. L</creator><creator>Horwell, D. C</creator><creator>Rank, W</creator><creator>Sano, T</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19920901</creationdate><title>Thermal and photochemical reactions of steroidal α-azido ketones</title><author>Edwards, O. E ; Douglas, J. L ; Horwell, D. C ; Rank, W ; Sano, T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c322t-1e45b4abf6e6ee415b3d697a4f61a3e4ccece030438fdc7b1e113fdecad65c7f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Edwards, O. E</creatorcontrib><creatorcontrib>Douglas, J. L</creatorcontrib><creatorcontrib>Horwell, D. C</creatorcontrib><creatorcontrib>Rank, W</creatorcontrib><creatorcontrib>Sano, T</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Edwards, O. E</au><au>Douglas, J. L</au><au>Horwell, D. C</au><au>Rank, W</au><au>Sano, T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thermal and photochemical reactions of steroidal α-azido ketones</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1992-09-01</date><risdate>1992</risdate><volume>70</volume><issue>9</issue><spage>2405</spage><epage>2412</epage><pages>2405-2412</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>Photolysis of 9α-azido-3β,20β-diacetoxy-5α-pregnan-11-one in methanol gave the N-acyl imine 11-aza-3β,20β-diacetoxy-C-homo-5α-pregn-9,11-en-12-one
4
and the aminoketone 9a-aza-3β,20β-diacetoxy-9-methoxy-B-homo-5α-pregnan-11-one
7
. In dichloromethane containing triethylamine the irradiation of this azide gave the N-acyl imine
4
and the α,β-unsaturated amino ketone 9a-aza-3β,20β-diacetoxy-B-homo-5α-pregn-8-en-11-one
8
. Thermolysis or photolysis of 12α-azido-3α,20β-diacetoxy-5β-pregnan-11-one gave the N-acyl imine 12-aza-3α,20β-diacetoxy-C-homo-5β-pregn-12-en-11-one
10
as major product. Photolysis of 20β-acetoxy-12α-azido-3α-hydroxy-5β-pregnan-11-one gave the 3-hydroxy analogue of
10
. Transformation products of the N-acyl imines are described.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v92-305</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| source | NRC Research Press; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| title | Thermal and photochemical reactions of steroidal α-azido ketones |
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