Tetrahedron

Photolytic ring-expansions of 6-azidoquinolines and 6-azidodiazines: some unexpected azepine ring-opening reactions

R Hayes, JM Schofield, RK Smalley, DIC Scopes

Index: Hayes, Roy; Schofield, Joseph M.; Smalley, Robert K.; Scopes, David I. C. Tetrahedron, 1990 , vol. 46, # 6 p. 2089 - 2096

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Citation Number: 6

Abstract

Photolysis of 6-azidoquianazoline in MeOH-KOMe-dioxan yields 8, 9-dihydro-5, 7- dimethoxy-5H-pyrimido [5, 4-] azepine (5) which on acid hydrolysis ring-opens to the pyrimidine-carbaldehyde (7). The mechanism of formation of this unexpected dimethoxypyrimido-azepine is discussed and related to previous similar results involving 6- azido-2, 3-dihydrofuro-and 6-azido-23-dihydrothieno-[2, 3-b] quinolines In contrast, 6- ...