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The synthesis of heterocycles from compounds of the indene series.

Barrett, Graham Campbell. (1959) The synthesis of heterocycles from compounds of the indene series. Doctoral thesis, University of Surrey (United Kingdom)..

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Known methods of thiazole formation have been applied to the novel syntheses of indeno-(1':2'-4:5)-thiazole, and its 2-methyl-, 2-phenyl-, 2-amino-, and 2-hydroxy-derivatives, from 2-bromoindan-l-one. The synthesis of 2-mercaptoindenothiazole has been investigated. Attempts have been made to obtain 3'-substituted derivatives of the more stable indenothiazoles, and 3'-oxo-, 3' -hydroxy-, and 3'-benzylidene-2-phenylindeno-(1':2'-4:5)-thiazole and 3'-benzylideneindeno-(1:2'-4:5)-thiazole have been prepared. The direct route to the 3'-oxo-indenothiazoles from 2-bromoindan-1:3-dione has on investigation proved unsuccessful. The syntheses from 2-bromoindan-l-one of indeno-(1':2'-4:5)-oxazole and its 2-methyl derivative, and of 2-methylindeno-(1':2'-4:5)-imidazole, have failed, the reactions resulting in conversion into 2:2-dibromoindan-l-one. 3'-Oxoindeno-(1':2'-3:2)-thiophen has been prepared by modification of a reported procedure; on reduction the ketone has yielded 3'-hydroxyindeno-(1':2'-3:2)-thiophen. The 3'-oxo-, 3' -hydroxy-, and 3'-benzylidene -indeno-heterocycles mentioned have been subjected to the azido-reaction in order, primarily, to synthesise quinolino- and isoquinolino-heterocycles; (iso )quinolono-(4' :3' -3 :2 )-thiophen, 2-phenyl(iso )quinolono-(4':3 '-4:5)-thiazole, and 2-phenyl- (iso)quinolino-(4' :3' -4 :5 )-thiazole have been so prepared. (isp)Quinolonothiophen and 2-phenyl(iso)quinolono-thiazole have been degraded by Raney nickel desulphurisation to 4-ethyl(iso)carbostyril and 4-benzylamino(iso)carbostyril respectively; a record is included of attempts to establish the structures of these latter compounds. The mechanism of the azido-reacticn is discussed. Ring-expansion by rearrangement of fluorenone hydrazone has been attempted.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
Barrett, Graham Campbell.
Date : 1959
Contributors :
Additional Information : Thesis (Ph.D.)--University of Surrey (United Kingdom), 1959.
Depositing User : EPrints Services
Date Deposited : 22 Jun 2018 13:56
Last Modified : 06 Nov 2018 16:53

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