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Morgan-Walls reaction

The Pictet-Hubert reaction describes the construction of the phenanthridine nucleus (2) by dehydration of acyl-o-xenylamines (1). The application of zinc chloride at high temperature facilitates the dehydration/ This reaction is also referred as the Morgan-Walls Reaction. [Pg.465]

Pictet-Hubert Reaction / Morgan-Walls Reaction... [Pg.506]

Badger and Sasse have described the preparation of 2-, 3-, and 8-bromophenanthridine by the cyclization of the appropriate bromo-formamidobiphenyl with polyphosphoric acid.25 In the case of 2-bromo-2 -formamidobiphenyl a higher concentration of phosphorus pentoxide in the acid was necessary to effect ring closure, and a simple steric effect was invoked.26 Nevertheless, the Morgan-Walls reaction has been used to obtain several overcrowded compounds in which unfavorable steric factors operate. Following the original report of the preparation of the 1,10-dimethylphenanthridine (5a) by this procedure,27 several other examples have been described, notably the synthesis of the related phenanthridine (5b),28 the l,2-(6)29 and 9,10-benzophenanthridines (7),30 and the 1,2 9,10-dibenzophenanthridine (8).29... [Pg.319]

The utility of the above method is again evident in the synthesis of 7,8-dimethoxy-phenanthridine which is not obtained by Morgan-Walls reaction. [Pg.130]

The Morgan-Walls reaction is a variant of the Pictet-Hubert reaction where the phenanthridine cyclization was accomplished by dehydrative ring closure of acyl-o-aminobiphenyls on heating with zinc chloride at 250—300 °C. [Pg.371]

Morgan-Walls reaction (Pictet-Hubert reaction)... [Pg.269]


See other pages where Morgan-Walls reaction is mentioned: [Pg.399]    [Pg.1971]    [Pg.371]    [Pg.413]    [Pg.11]    [Pg.16]    [Pg.269]    [Pg.241]    [Pg.371]   
See also in sourсe #XX -- [ Pg.399 ]

See also in sourсe #XX -- [ Pg.371 ]

See also in sourсe #XX -- [ Pg.413 ]

See also in sourсe #XX -- [ Pg.269 ]

See also in sourсe #XX -- [ Pg.241 ]

See also in sourсe #XX -- [ Pg.371 ]




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