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6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions

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Abstract

6,7-Dimethoxy-3,4-dihydroisoquinolin-1-ylacetonitrile in the enamine form readily reacts with acyl iso(thio)cyanates affording in high yields 1,2-fused oxo- and thioxodihydropyrimidoisoquinolines and thiouracyloisoquinolines. The reaction of the enamine with primary amines of diverse classes in the presence of 2 equiv of formaldehyde resulted in 1,2-fused N-substituted tetrahydropyrimidinoisoquinolines whose yields depended on the basicity and sterical accessibility of the reagent. Fused 5-hydroxyindolo-, dioxopyrrolo-, pyrroloisoquinolines formed in medium yields in the one-stage reactions of the enamine with p-benzoquinone, oxalyl chloride, and β-nitrostyrene respectively. The reaction of 1-cyanomethyl-6,7-dimethoxydihydroisoquinoline with acrylonitrile leads to the formation of 1,2-fused iminopyridinoisoquinoline easily hydrolysable to pyridine derivative and readily reacting by the amidine group with aroyl chlorides and arylsulfonyl chlorides.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk, 83114, Ukraine

    A. A. Afon’kin, M. L. Kostrikin, A. E. Shumeiko & A. F. Popov

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  1. A. A. Afon’kin
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  2. M. L. Kostrikin
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  3. A. E. Shumeiko
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  4. A. F. Popov
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Correspondence to A. A. Afon’kin.

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Original Russian Text © A.A. Afon’kin, M.L. Kostrikin, A.E. Shumeiko, A.F. Popov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 726–740.

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Afon’kin, A.A., Kostrikin, M.L., Shumeiko, A.E. et al. 6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions. Russ J Org Chem 47, 731–745 (2011). https://doi.org/10.1134/S1070428011050137

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