Some studies of substituted pyridine and quinoline compounds

Crawforth, Colin Edward (1971) Some studies of substituted pyridine and quinoline compounds. Doctoral thesis, Harris College.

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The reactions with tpioolia G with lepidSas have beci investigated 0 The conditions flewià for eztensivs thfl gflap litigation, fl 09)0504 to -the alterlu tin Ompas=thine S4itiov reaction, are dstsrmigis4 and the results are die *8004 a With leptUivt
mnsazththe a"Itiog was predSisM, although litatioU at the 4,40thA grmsp by planflalithiun was for the first tire auwSfnlly accolisSd.
MdStioa of omthyl beaoete to the thtnaefleW res ection products at v]Sflfl4ittium and the sbflt lwtfloc1io • bates gave., With 4plcoflna, acflated products teaultins twos stteck at the lithiate8 ntbfl aup. With lopidile however, a sofa prSct was formed which to formulated as dipbnfle 2aQtsznethflquinolfl) mathand. The araalagotw qjatnoriiS cpouM was siatlafly $ovred, £fl&0900 is presented 8btCh suggeata that these compounds are ttned by attack at methyl bensoato on a Sam ' eltthtn2spMflle ,2.dibydroquSAOlin* $Ateniediate.
An alterustin route to these end the wlogmzs di- ~enfl-24 (1.aethflpyrs4fl )asthenol • involving the ha to racwolic bass. Lithium metal end bonaophenone tee discovend. when the Mtenaelio bases were qutsealine, quSceJAiae, 2 ,6edSztbflinolins, 2-phenyiquinolinS, 6eeathfl-2sphtflltzolixa and 8.thfl-2-pheaflqa'iiDs, nsv products,
formulated as substituted k,Ls.4iplienfl-1 ,2,h,5tetnhtdt* 2Ø, methanosj,$-benaezazspine, were isolated. These solids gave
the correapwzding Is(dSheny1mcttfl)quSn61tnts (th.aelvts an ccapaunfle} when trnted with 70$ sulphuric acid at
Beto:, Part ct this .vovk, entitled, 'A Lithium Analdgtxe of the kert Reaction' has been publtohe40 tcaa, 1970, 1106, (See Appethix (liz)).

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