Abstract
High yields of 3-acylamino-2-benzopyrylium salts are formed in the acylation of 3,4-dimethoxy- and 3,4-methylenedioxyphenylacetonitrile. The salts are converted to 4-isoquinolones on treatment with ammonia. The acylation of ethyl 3,4-dimethoxyphenylglycidate ester also results in heterocyclization to 3-carbethoxy-2-benzopyrylium salts, which are converted to high yields of the corresponding 3-carbethoxyisoquinolines by treatment with ammonium hydroxide. The mechanisms of these transformations are discussed.
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G. N. Dorofeenko, L. V. Dulenko, V. I. Dulenko, and S. V. Krivun, Zh. Organ. Khim., 1, 1171 (1965).
G. N. Dorofeenko, E. V. Kuznetsov, and S. V. Krivun, Zh. Organ. Khim., 2, 1499 (1966).
G. N. Dorofeenko, V. G. Korobkova, and S. V. Krivun, USSR Author's Certificate No. 207,921 (1967); Byull. Izobr., No. 3 (1967).
A. Muller and A. Horvath, Ber., 75, 891 (1942).
M. Vajda, Acta Chim. Hung., 40, 295 (1964).
West German Patent No. 937,589 (1956); Chem. Abstr., 53, 3250g (1959).
G. N. Dorofeenko, E. I. Sadekova, S. V. Krivun, S. N. Baranov, and V. I. Dulenko, USSR Author's Certificate No. 269,436 (1968); Byull. Izobr., No. 14 (1970).
G. N. Dorofeenko, V. G. Korobkova, and S. V. Krivun, Khim. Geterotsikl. Soedin., No. 2, 200 (1970).
M. S. Newman and B.G. Majorlein, Organic Reactions, Vol. 5 [Russian translation], IL, Moscow (1951), p. 319.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 730–732, June, 1971.
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Dorofeenko, G.N., Krivun, S.V. & Sadekova, E.I. Synthesis of 3-acylamino- and 3-carbethoxy-2-benzopyrylium salts. Chem Heterocycl Compd 7, 681–683 (1971). https://doi.org/10.1007/BF00476805
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DOI: https://doi.org/10.1007/BF00476805