Synthesis of 10-substituted-3,4,10,10a-tetrahydro-2H-1,9-dioxa-4aazaphenanthrenes | Abstract

Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

ISSN: 0975-413X
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Synthesis of 10-substituted-3,4,10,10a-tetrahydro-2H-1,9-dioxa-4aazaphenanthrenes

Author(s): V. Rajachandrashekar*, B. George Vineel, S. Venkataiah and P. K. Dubey

Commercially available 2-nitrophenol 1 was treated with ethyl bromoacetate to obtain the (2-ntrophenoxy)acetic acid ethyl ester (2). Then, 2 was reduced with Fe/AcOH to yield 4H-benzo[1,4]oxazin-3-one (3), which on treatment with ethyl 3-bromopropionate led to the formation of 3-(3-oxo-2,3-dihydrobenzo[1,4]oxazin-4–yl)propionic acid ethyl ester (4). Reduction of 4 with lithium aluminiumhydride gave 3,4,10,10a–tetrahydro-2H-1,9-dioxa-4aazaphenanthrene (5). All the new products obtained in the above sequences of reactions have been adequately characterized by spectral data


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