A new class of phtalimido-quinones sinthesys

<p><em>Four new Michael adducts from the reaction between 1,4-naphthoquinone and 2,3-dibromo-1,4-naphthoquinone with w-amino-N-alkylphthalamide derivatives were presented in this work (Scheme 1). The products named 2a-c were completed assigned on the basis of <sup>13</sup>C,...

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Bibliographic Details
Main Authors: Jeziane S. Alves, Josinete A. Paz, Celso A. Camara
Format: Article
Language:English
Published: Universidade Federal de Mato Grosso do Sul 2012-06-01
Series:Orbital: The Electronic Journal of Chemistry
Subjects:
Online Access:http://orbital.ufms.br/index.php/Chemistry/article/view/357
Description
Summary:<p><em>Four new Michael adducts from the reaction between 1,4-naphthoquinone and 2,3-dibromo-1,4-naphthoquinone with w-amino-N-alkylphthalamide derivatives were presented in this work (Scheme 1). The products named 2a-c were completed assigned on the basis of <sup>13</sup>C, <sup>1</sup>HNMR, IR and elemental analysis, still remaining spectroscopy data of 3a product (n=4). The global yields of 2a-c (n=3, 4 e 6) and 3a(n=4), was respectively  41%, 39 %, 27% and 30%.The yields are low probably due the formation of dimeric by-products. A new methodology has been employed to obtain the key-intermediates</em><em> </em><em>w-amino-N-alkylphthalamide (4a-b), using bromide alkylphthalamide (6a-b) (n=3-4) to obtain the corresponding azides (5a-b) with 85% and 90% yields, followed by catalytic hydrogenation with the use of palladium on charcoal 10 % to obtain w-amino-N-alkylphthalamide (4a-b) with respectively 90% e 60% yields, as a more viable synthesis route. </em><strong><em></em></strong></p>
ISSN:1984-6428