Synthesis and structure of tricyclic quinazoline alkaloid oxalates |
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Authors: | A. G. Tozhiboev K. K. Turgunov B. Tashkhodzhaev Kh. M. Shakhidoyatov |
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Affiliation: | (1) S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, prosp. Akad. Kh. Abdullaeva, 77 |
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Abstract: | Oxalates of the alkaloids deoxyvasicinone, 2,3-tetra-, and their seven-membered analog 2,3-pentamethylen-3,4-dihydroquinazol-4-one and the complex of 2,3-pentamethylen-3,4-dihydroquinazol-4-one hydrochloride with oxalic acid were synthesized. It was found that 2:1, 2:1, and 1:1 alkaloid:oxalic acid complexes, respectively, were formed. The last complex had 2,3-pentamethylen-3,4-dihydroquinazol-4-one, oxalic acid, and HCl in a 2:1:2 ratio, respectively. X-ray crystal structures of single crystals were performed. The oxalate of 2,3-pentamethylen-3,4-dihydroquinazol-4-one and its hydrochloride formed salts with a protonated N1 atom and involvement of only one hydroxyl. The other alkaloids formed a complex with oxalic acid through N1…H-O H-bonds involving both acid hydroxyls. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 152–156, March–April, 2007. |
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Keywords: | deoxyvasicinone 2,3-tetra-,-pentamethylene-3,4-dihydroquinazol-4-one oxalates x-ray crystal structure complexes protonation H-bonds |
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