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Synthesis 2010(19): 3374-3378  
DOI: 10.1055/s-0030-1257973
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Annulated Pyrroles: Condensation of Aldose Sugars, Arylamines, and 1,3-Diones Using TBAB

Lingaiah Nagarapu*, Venkata Narasimhaji Cheemalapati, Shuklachary Karnakanti, Rajashaker Bantu
Organic Chemistry Division-II, Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, India
Fax: +91(40)27193382; e-Mail: nagarapu2@yahoo.co.in; e-Mail: nagarapu@iict.res.in;
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Publication History

Received 15 May 2010
Publication Date:
13 August 2010 (online)

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Abstract

Readily available tetrabutylammonium bromide (TBAB, 10 mol%), in the molten state, efficiently catalyzes the reaction of a variety of in situ generated enamines, from arylamines and 1,3-ketones, with aldose sugars under solvent-free conditions. The reaction proceeds rapidly and affords the corresponding protected annulated pyrrole derivatives in good to high yields (55-78%) after acetylation. The present methodology offers advantages such as excellent yields, a simple procedure, shorter reaction times, and milder conditions.

Key words

aldose sugars - 1,3-diones - tetrabutylammonium bromide - one-pot synthesis - shorter reaction times

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