Beilstein J. Org. Chem.2007,3, No. 10, doi:10.1186/1860-5397-3-10
Marjit W. Singh Anirban Karmakar Nilotpal Barooah Jubaraj B. Baruah Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039 Assam, India 10.1186/1860-5397-3-10 Abstract Reaction of 1,2-naphthoquinone with primaryamines gives a 2-amino-1,4-naphthoquinone derivative
-benzoquinone reacts with primaryamines to give 2,5-diamino 1,4-benzoquinones; similar reaction of 1,4-naphthoquinone with primaryamines results in the formation of 2-amino 1,4-naphthoquinones. [13] However, the product formed from such simple reaction of amine with various quinones has much scope for
exploration, especially in terms of synthesis of electro/photoactive supramolecular assemblies or polymers. In this communication we describe preliminary account of results obtained on the equivalence of reaction of 1,2-naphthoquinone and 1,4-naphthoquinone with primaryamines.
Results and discussion
It is
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Graphical Abstract
Scheme 1:
Reaction of 1,2-naphthoquinone with primary amines.
Beilstein J. Org. Chem.2005,1, No. 12, doi:10.1186/1860-5397-1-12
side of the bulky TBDMS group in β-position. However, it has to be pointed out that more hindered nucleophiles, such as primaryamines, revealed unable to open the cyclic sulfate 9 or 10.
The absolute configurations of 11 and 12 were established by NMR studies. 1H signals were assigned (Table 1) using