2-(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinone

Details 2-(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinone 2-(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinone

1989-02-15

1990-12-25

Garner, Vivian

Organic compounds -- part of the class 532-570 series

Organic compounds

Cyclohexadiene having atoms double bonded directly at the 1-...

C07C22524

Patent

active

049804898

ABSTRACT:
A 2-(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinone of the formula: ##STR1## wherein R.sup.1 is an alkyl group or a cycloalkyl group, and R.sup.2 is an alkyl group having at least 2 carbon atoms.
The compounds are used in the preparation of a 2-(1-alkenyl)-3-hydroxy-1,4-naphthoquinone having insecticidal and fungicidal activity and a 2-alkyl-3-acyloxy-1,4-naphthoquinone having insecticidal and fungicidal activity and a 2-alkyl-3-acyloxy-1,4-naphthoquinone having miticidal activity.

REFERENCES:
patent: 2541473 (1951-02-01), Leffler
patent: 2553647 (1951-05-01), Fieser et al.
patent: 4110473 (1978-08-01), Fugitt et al.
Journal of the Amer. Chem. Society, vol. 71, May, 1949, pp. 1697-1702; C. E. Dalgliesh: "Naphthoquinone Antimaterials. Mannich Bases Derived from Lawsone".
Journal of the Chem. Society, Perkin Transactions I, 1986, pp. 659-664; K. Bock et al., "Reaction of 2-Hydroxy-1,4-naphthoquinone with aldehydes. Synthesis of 2-Hydroxy-3-alk-1-enylnaphthoquinones".
Journal of the Amer. Chem. Society, vol. 58, Jul., 1936, pp. 1163-1167; S. C. Hooker: "Condensation of Aldehydes with Beta-Hydroxy-alpha-naphthoquinone, Synthesis of Hydrolapachol".
Chemical Abstracts, vol. 94, No. 23, Jun. 8, 1981, p. 625, Column 2, Abstract No. 191985y, Columbus, Oh., G.-L. XI et al.; "Studies on Antiasthmatic Agents, II. Synthesis of some Omega-(e-hydroxyl-1,4-naphthoquinonyl-2)-alkanoic acids and Mannich bases of 2-hydroxy-1,4-naphthoquinone"& Yao Hsueh Hsueh Pao 1980, vol. 15, No. 9, pp. 548-554.
Chemical Abstracts, vol. 78, No. 7, Feb., 1973, p. 549, column 2, Abstract No. 43130v, Columbus, Oh., U.S.A.; JP-A-72 029353.
Leffler, M. T. et al., J. Amer. Chem. Soc., 70, 3222 (1948).
Dalglish, C. E., J. Amer. Chem. Soc., 71, 1697 (1944).
Fieser, L. T. et al. J. Am. Chem. Soc., 70, 3156 (1948).

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