Synthesis, characterization, and thermolysis of 7-amino-7-azabenzonorbornadienes

LA Carpino, RE Padykula, DE Barr…

Index: Carpino, Louis A.; Padykula, Robert E.; Barr, Donald E.; Hall, Frances H.; Krause, Josef G.; et al. Journal of Organic Chemistry, 1988 , vol. 53, # 11 p. 2565 - 2572

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Citation Number: 50

Abstract

Synthetic routes are given for the facile preparation of mono-and dibenzo-7-amino-7- azanorbornadienes 4 and 5. For 5 the key intermediate N-benzylisoindole (9) was treated with benzyne, generated via reaction of o-bromofluorobenzene with magnesium in THF to give tertiary amine 10. N-Bromosuccinimide-mediated debenzylation of 10 gave secondary amine 13, which was then aminated by 0-(mesitylsulfony1) hydroxylamine (MSH). ...