Synthesis and structure of 6-bromo-4-hydroxy-2,3-tetramethylene-3,4-dihydroquinazoline and its mixed crystal with 4-hydroxy-2,3-tetramethylene-3,4-dihydroquinazoline

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• 作者：N. I. Mukarramov ; R. Ya. Okmanov ; F. R. Utaeva ; K. K. Turgunov ; B. Tashkhodzhaev ; Z. M. Khakimova and Kh. M. Shakhidoyatov
• 关键词：alkaloids ; quinazolines ; co ; crystals ; bromination ; N ; bromosuccinimide ; oxidation ; KMnO4 ; x ; ray structure analysis
• 刊名：Chemistry of Natural Compounds
• 出版年：2009
• 出版时间：November, 2009
• 年：2009
• 卷：45
• 期：6
• 页码：854-858
• 全文大小：146.7 KB

文摘

Bromination of the alkaloid 2,3-tetramethylene-3,4-dihydroquinazoline by N-bromosuccinimide was studied. It was shown that either 4-hydroxy-2,3-tetramethylene-3,4-dihydroquinazoline or 6-bromo-4-hydroxy-2,3tetramethylene-3,4-dihydroquinazoline was formed depending on the ratio of reagents. Oxidation of 2,3tetramethylene-3,4-dihydroquinazoline by KMnO₄ produced 4-hydroxy-2,3-tetramethylene-3,4dihydroquinazoline. The crystal structures of 6-bromo-4-hydroxy-2,3-tetramethylene-3,4-dihydroquinazoline and its mixed crystal with 4-hydroxy-2,3-tetramethylene-3,4-dihydroquinazoline were studied by x-ray structure analysis. The enantiomeric molecules in all crystal structures formed associates owing to two opposing OH...N1 H-bonds.