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Directions of reactions of 6-amino-, -acetylamino-, and -benzoylaminodeoxyvasicinones with aldehydes

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Chemistry of Natural Compounds Aims and scope

6-Acetylamino- and -benzoylamino-9-arylidenedeoxyvasicinones were synthesized by reaction of 6-amino(3), -acetylamino- (4), and -benzoylamino- (5) -deoxyvasicinones (DOV) with aromatic aldehydes and furfurol in glacial acetic acid. It was shown that the amino group of 6-aminodeoxyvasicinone underwent acylation upon reaction with aldehydes to form 6-acetylamino-DOV, which reacted with aldehydes to form 9-arylidene derivatives. Carrying out this condensation in toluene, o-xylene, and ethanol produced a mixture of condensation products at the 6-amino-and a-CH2-groups. It was found that condensati on of 3 with 4-nitrobenzaldehyde in pyridine formed exclusively the Schiff bases. Methods for preparing 6-nitrodeoxyvasicinone and for its reduction were improved.

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Acknowledgment

The work was supported financially by Basic Research TsNT RUz (Project No. FA-F3-T047).

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Authors and Affiliations

  1. S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Republic of Uzbekistan

    B. Zh. Elmuradov, A. Sh. Abdurazakov & Kh. M. Shakhidoyatov

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  1. B. Zh. Elmuradov
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  2. A. Sh. Abdurazakov
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  3. Kh. M. Shakhidoyatov
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Correspondence to B. Zh. Elmuradov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 220–225, March–April, 2010.

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Elmuradov, B.Z., Abdurazakov, A.S. & Shakhidoyatov, K.M. Directions of reactions of 6-amino-, -acetylamino-, and -benzoylaminodeoxyvasicinones with aldehydes. Chem Nat Compd 46, 262–267 (2010). https://doi.org/10.1007/s10600-010-9583-8

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