A new class of phthalimido-quinones synthesis

Orbital: The Electronic Journal of Chemistry

Josinete A. Paz¹  Celso A. Camara¹  Jeziane S. Alves¹ 

[1] Departamento de Ciências Moleculares, Universidade Federal Rural de Pernambuco;

关键词: quinones;    phthalimides;    michael addition;   

DOI  :  10.17807/orbital.v4i1.342

来源: DOAJ

【 摘 要 】

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. The products named 2a-c were completed assigned on the basis of ¹³C, ¹HNMR, 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 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.

【 授权许可】

Unknown