Synthesis and structure verification of an analogue of kuanoniamine A

…, S Lawrence, DJ Williams, YA Jackson

Index: Lyon, Michael A.; Lawrence, Simon; Williams, David J.; Jackson, Yvette A. Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 4 p. 437 - 442

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Citation Number: 38

Abstract

Synthesis of 9-phenyl-7H-benzothiazolo [4, 5, 6-ij][2, 7] naphthyridin-7-one 11, an analogue of kuanoniamine A 8, is described. The synthesis involves a hetero Diels–Alder reaction of crotonaldehyde dimethylhydrazone with 4, 7-dioxo-2-phenylbenzothiazole 18a or with 6- bromo-4, 7-dioxo-2-phenylbenzothiazole 18b followed by annelation of the appropriate adduct. Reaction with 18a produced two sets of regioisomers—the ...