An efficient and convenient synthesis of tetrahydrocycloheptapyridines: New precursors for CNS agents

Development of a convenient and efficient synthetic route for functionalized tetrahydrocycloheptapyridines was accomplished by stepwise iodomethylation and subsequent radical ring expansion using a BU3SnH/AIBN reaction system. Thus, 8- or 5-oxotetrahydroquinolines 4a and 4d and 8- or 5-oxotetrahydro...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 10; pp. 1593 - 1600
Main Authors Yoshizumi, T, Miyazoe, H, Sugimoto, Y, Takahashi, H, Okamoto, O
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
(AMINOALKYL)BENZO
RECEPTOR ANTAGONISTS
RING-EXPANSION
ANALOGS
radical reaction
BETA-KETO-ESTERS
hydroxymethylation
BUTYROPHENONE
DINUCLEOPHILES
ring expansion
PHARMACOLOGY
iodomethylation
cycloheptanone
2-DIMETHYLAMINOMETHYLENE-1,3-DIONES
DERIVATIVES
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Summary:Development of a convenient and efficient synthetic route for functionalized tetrahydrocycloheptapyridines was accomplished by stepwise iodomethylation and subsequent radical ring expansion using a BU3SnH/AIBN reaction system. Thus, 8- or 5-oxotetrahydroquinolines 4a and 4d and 8- or 5-oxotetrahydroisoquinolines 4b and 4c afforded the 5,6,7,8-tetrahydrocycloheptapyridine-9-ones 3a and 3d and 6,7,8,9-tetrahydrocycloheptapyridine5-ones 3b and 3c, respectively, in moderate total yields (37-61%). It was also found out that this reaction sequence was applicable to the preparation of other heterocyclic fused cycloheptanones.
ISSN:0039-7881
DOI:10.1055/s-2005-865306