Synthesis and reactions of some dihydro and tetrahydro??4H??imidazo [5, 4, 1??ij] quinoline derivatives

WS Saari, W Halczenko, MB Freedman…

Index: Saari, Walfred S.; Halczenko, Wasyl; Freedman, Mark B.; Arison, Byron H. Journal of Heterocyclic Chemistry, 1982 , vol. 19, p. 837 - 840

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Citation Number: 4

Abstract

Abstract Reaction of phenyl N-(8-quinolinyl) carbamate with sodium borohydride afforded 1, 2-dihydro-4H-imidazo-[5, 4, 1-ij] quinolin-2-one, 2a. The 5, 6-double bond of 2a was functionalized by reaction with nitrosyl chloride to give the nitroolefin 4 and by reaction with hypobromous acid to give the trans-bromohydrin 5. Reaction of 5 with sodium azide led to the rearranged trans-6-azido-5-ol 7, the structure of which was determined by 1 H nmr ...