Synthesis and reactions of 10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones
Cyclocondensation of 2,3,3‐trimefhyl‐3 H ‐indoles 2 with malonates 3 gives 8‐hydroxy‐10,10‐dimefhyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones 4 , which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10 H ‐pyrido[1,...
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| Veröffentlicht in: | Journal of heterocyclic chemistry 2002-03, Vol.39 (2), p.391-397 |
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| container_issue | 2 |
| container_start_page | 391 |
| container_title | Journal of heterocyclic chemistry |
| container_volume | 39 |
| creator | Kappe, Thomas Frühwirth, Franz Roschger, Peter Jocham, Brigitte Kremsner, Jenny Stadlbauer, Wolfgang |
| description | Cyclocondensation of 2,3,3‐trimefhyl‐3
H
‐indoles
2
with malonates
3
gives 8‐hydroxy‐10,10‐dimefhyl‐10
H
‐pyrido[1,2‐
a
]indol‐6‐ones
4
, which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10
H
‐pyrido[1,2‐
a
]indoles
5, 6, 7
and
8
. Amination affords the 8‐amino‐10,10‐dimethyl‐10
H
‐pyrido[1,2‐
a
]indol‐6‐one
9
. Nitration gives either the 10,10‐dimethyl‐7‐nitro‐10
H
‐pyrido[1,2‐
a
]indoles
10
or 10,10‐dimethyl‐7‐hydroxy‐10
H
‐pyrido[1,2‐
a
]indoles
11
, depending on the conditions. |
| doi_str_mv | 10.1002/jhet.5570390224 |
| format | Article |
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H
‐indoles
2
with malonates
3
gives 8‐hydroxy‐10,10‐dimefhyl‐10
H
‐pyrido[1,2‐
a
]indol‐6‐ones
4
, which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10
H
‐pyrido[1,2‐
a
]indoles
5, 6, 7
and
8
. Amination affords the 8‐amino‐10,10‐dimethyl‐10
H
‐pyrido[1,2‐
a
]indol‐6‐one
9
. Nitration gives either the 10,10‐dimethyl‐7‐nitro‐10
H
‐pyrido[1,2‐
a
]indoles
10
or 10,10‐dimethyl‐7‐hydroxy‐10
H
‐pyrido[1,2‐
a
]indoles
11
, depending on the conditions.</description><identifier>ISSN: 0022-152X</identifier><identifier>EISSN: 1943-5193</identifier><identifier>DOI: 10.1002/jhet.5570390224</identifier><language>eng</language><ispartof>Journal of heterocyclic chemistry, 2002-03, Vol.39 (2), p.391-397</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c864-d5702da1ab511edaf74d9d1a86e35606f9337a31b78ddf2d5da406ef718512c93</citedby><cites>FETCH-LOGICAL-c864-d5702da1ab511edaf74d9d1a86e35606f9337a31b78ddf2d5da406ef718512c93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Kappe, Thomas</creatorcontrib><creatorcontrib>Frühwirth, Franz</creatorcontrib><creatorcontrib>Roschger, Peter</creatorcontrib><creatorcontrib>Jocham, Brigitte</creatorcontrib><creatorcontrib>Kremsner, Jenny</creatorcontrib><creatorcontrib>Stadlbauer, Wolfgang</creatorcontrib><title>Synthesis and reactions of 10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones</title><title>Journal of heterocyclic chemistry</title><description>Cyclocondensation of 2,3,3‐trimefhyl‐3
H
‐indoles
2
with malonates
3
gives 8‐hydroxy‐10,10‐dimefhyl‐10
H
‐pyrido[1,2‐
a
]indol‐6‐ones
4
, which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10
H
‐pyrido[1,2‐
a
]indoles
5, 6, 7
and
8
. Amination affords the 8‐amino‐10,10‐dimethyl‐10
H
‐pyrido[1,2‐
a
]indol‐6‐one
9
. Nitration gives either the 10,10‐dimethyl‐7‐nitro‐10
H
‐pyrido[1,2‐
a
]indoles
10
or 10,10‐dimethyl‐7‐hydroxy‐10
H
‐pyrido[1,2‐
a
]indoles
11
, depending on the conditions.</description><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNpFkFFLwzAUhYMoWKfPvuYHrFtu0iTNowx1wsAHBwoiJetNaMfWjqQvffMn-Bv9JaYo-HA598DhcPgIuQW2AMb4ct-4YSGlZsIwzoszkoEpRC7BiHOSpQTPQfK3S3IV4z5ZEFpn5PVl7IbGxTZS2yENztZD23eR9p4CmwP7_vzC9uiGZjykFxhd06SnMbTYv8OcJ0Mt_Wg77KeAStd3Ll6TC28P0d386YxsH-63q3W-eX58Wt1t8rpURY5pLkcLdicBHFqvCzQItlROSMWUN0JoK2CnS0TPUaItmHJeQymB10bMyPK3tg59jMH56hTaow1jBayasFQTluofi_gBsYRabQ</recordid><startdate>200203</startdate><enddate>200203</enddate><creator>Kappe, Thomas</creator><creator>Frühwirth, Franz</creator><creator>Roschger, Peter</creator><creator>Jocham, Brigitte</creator><creator>Kremsner, Jenny</creator><creator>Stadlbauer, Wolfgang</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200203</creationdate><title>Synthesis and reactions of 10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones</title><author>Kappe, Thomas ; Frühwirth, Franz ; Roschger, Peter ; Jocham, Brigitte ; Kremsner, Jenny ; Stadlbauer, Wolfgang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c864-d5702da1ab511edaf74d9d1a86e35606f9337a31b78ddf2d5da406ef718512c93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kappe, Thomas</creatorcontrib><creatorcontrib>Frühwirth, Franz</creatorcontrib><creatorcontrib>Roschger, Peter</creatorcontrib><creatorcontrib>Jocham, Brigitte</creatorcontrib><creatorcontrib>Kremsner, Jenny</creatorcontrib><creatorcontrib>Stadlbauer, Wolfgang</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kappe, Thomas</au><au>Frühwirth, Franz</au><au>Roschger, Peter</au><au>Jocham, Brigitte</au><au>Kremsner, Jenny</au><au>Stadlbauer, Wolfgang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and reactions of 10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><date>2002-03</date><risdate>2002</risdate><volume>39</volume><issue>2</issue><spage>391</spage><epage>397</epage><pages>391-397</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>Cyclocondensation of 2,3,3‐trimefhyl‐3
H
‐indoles
2
with malonates
3
gives 8‐hydroxy‐10,10‐dimefhyl‐10
H
‐pyrido[1,2‐
a
]indol‐6‐ones
4
, which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10
H
‐pyrido[1,2‐
a
]indoles
5, 6, 7
and
8
. Amination affords the 8‐amino‐10,10‐dimethyl‐10
H
‐pyrido[1,2‐
a
]indol‐6‐one
9
. Nitration gives either the 10,10‐dimethyl‐7‐nitro‐10
H
‐pyrido[1,2‐
a
]indoles
10
or 10,10‐dimethyl‐7‐hydroxy‐10
H
‐pyrido[1,2‐
a
]indoles
11
, depending on the conditions.</abstract><doi>10.1002/jhet.5570390224</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-152X |
| ispartof | Journal of heterocyclic chemistry, 2002-03, Vol.39 (2), p.391-397 |
| issn | 0022-152X 1943-5193 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_jhet_5570390224 |
| source | Access via Wiley Online Library |
| title | Synthesis and reactions of 10,10‐dimethyl‐10 H ‐pyrido[1,2‐ a ]indol‐6‐ones |
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