1-(substituted benzyl)-3-(substituted aryl)-condensed pyrazole d

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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5483611, 5483625, C07D23156, C07D48704

Patent

active

055741681

ABSTRACT:
The invention pertains to a process for preparing (1-substituted benzyl)-3-(hydroxy-carbonyl aryl) condensed pyrazoles or (1-substituted benzyl)-3-(hydroxymethyl aryl) condensed pyrazoles comprising the steps of: (a) reacting compound I and compound II, or compound III and compound IV, to produce compound V, which is a substituted aryl ketone, as follows: ##STR1## wherein Ar.sub.2 and At.sub.3 can be, independently, ##STR2## R.sub.1 is H, C.sub.1-3 alkyl, or X (halogen), R.sub.3 is H, C.sub.1-3 alkyl, X (halogen), or --OR radical, and R is H or C.sub.1-3 alkyl; the process comprising the following steps of: R.sub.2 represents CH.sub.2 OR, H, COOR, C.sub.1-3 alkyl, or X (halogen); (b) reacting the compound V with a hydrazine compound to form a hydrazone compound; (c) reacting the hydrazone compound compound with trifluoride etherate (BF.sub.3 .cndot.Et.sub.2 O) to form a 1-(substituted benzyl) 3-(substituted aryl) condensed pyraxzole, which is represented by the following formula of ##STR3## Compound X can be further hydrolyzed or reduced to form corresponding carboxylic acids or alcohols.

REFERENCES:
Yoshina et al. Yakugaku Zasshi (5)1977, 97(9) pp. 955-961.
Yoshina et al. Yakugaku Zasshi (5)1978, 98(2), pp. 204-209.
Streitwieser et al. "Introduction to Organic Chemistry " 3rd Ed(8)1985 by Macmillan Publishing Company (New York) pp. 449-506.

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