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Adamantyl-containing heterocycles Communication 1. 3-(1-adamantyl)-3-chloropropenal in the synthesis of 2-(1-adamantyl)thiophene and 5-(1-adamantyl)isoxazole

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    By the action of POCl3 and DMF on (1-adamantyl)methylketone, we obtain the trans Z isomer of 3-(l-adamantyl)-3-chloropropenal, which is a convenient synthon for synthesis of heteryl adamantanes.

  2. 2.

    By the reaction of 3-(1-adamantyl)-3-chloropropenal with thioglycolic acid, we obtain 2-(1-adamantyl)-thiophene and the corresponding 5-carboxylic acid; with hydroxyl amine we obtain 5-(1-adamantyl)isoxazole.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    V. P. Litvinov, V. S. Dermugin, V. I. Shvedov & V. S. Bogdanov

Authors
  1. V. P. Litvinov
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  2. V. S. Dermugin
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  3. V. I. Shvedov
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  4. V. S. Bogdanov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1581–1585, July, 1984.

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Litvinov, V.P., Dermugin, V.S., Shvedov, V.I. et al. Adamantyl-containing heterocycles Communication 1. 3-(1-adamantyl)-3-chloropropenal in the synthesis of 2-(1-adamantyl)thiophene and 5-(1-adamantyl)isoxazole. Russ Chem Bull 33, 1451–1455 (1984). https://doi.org/10.1007/BF00956524

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  • DOI: https://doi.org/10.1007/BF00956524

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