Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-10-01
1995-10-31
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
558 83, 558411, 568442, 568630, 568631, 560 55, 562471, 564 52, 564 53, 564218, C07F 906
Patent
active
054630592
ABSTRACT:
A process for preparing compounds of the formula ##STR1## where a, b, c, R.sub.1, R.sub.2, and R.sub.3 are as defined herein including the step of alkylating a phenol of formula ##STR2## with an acetylene of formula ##STR3## where X is chlorine; bromine; --OC(O)--R.sub.5, where R.sub.5 is alkyl, aryl or substituted aryl; or --OCO.sub.2 R.sub.6, where R.sub.6 is alkyl or ##STR4## in the presence of a catalytic amount of a cuprous or cupric salt. The compounds of formula I are intermediates useful in the preparation of pyranyl cyanoguanidine derivatives.
REFERENCES:
patent: 4545993 (1985-10-01), Okamoto et al.
patent: 5140031 (1993-08-01), Atwal et al.
R. W. Lang et al., "67. Synthesis of Selectively Trifluoromethylated Pyrridine Derivatives as Potential Antihypertensives", Helvetica Chemica Acta, 71, (1988), 596-601.
P. Barmettler et al., 140. Acid-Catalyzed [3,3]-Sigmatropic Rearrangements of N-Propargylanilines, Helvetica Chimica Acta, 1990; 73:1515-1573.
G. F. Hennion et al., The Alkylation of Amines with t-Acetylenic Chlorides. Preparation of Sterically Hindered Amines, JACS, 1960;82:4908-4912.
A. Caporusso et al., Copper Catalyzed Aminolysis of Bromoallenes as a New Efficient Route to Propargylamines, Tet. Lett., 1991;7471-7472.
A. J. Bridges, Phenylthiocopper Trimethylphosphite Complex. A Reagent for the Preparation of Thioallenes, Tet. Lett., 1980;21:4401-4404.
S. C. Joshi et al., A Study Of Claisen Rearrangements Of(1,1-Dimethyl-3-Prop-2-Ynyloxy)-[4H]-1-Benzopyran-4-One Derivatives, Tet. Lett., 1992;48:563-565.
R. D. Murray et al, Synthesis of the Coumarins, Avicennol, Dipetaline and Dipetalolactone, Tet. Lett., 1976;12:953-954.
M. Harfenist et al., The Influence of Structure on the Rate of Thermal Rearrangement of Aryl Propargyl Ethers to the Chromenes. The gem-Dimethyl Effect, J. Org. Chem., vol. 37, 1972;6:841-848.
J. M. Evans et al., Synthesis and Antihypertensive Activity of Substituted trans-4-Amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols, J. Med. Chem., 1983;26:1582-1589.
F. Bohlmann et al., Synthese von naturlich vorkommenden Hydroxyacetophenon-Derivaten, Chem. Ber., 1972;105:863-873.
S. C. Joshi et al., A Study of Several Claisen Rearrangements, Tetrahedron, 1992;48:566-570.
Godfrey Jr. Jollie D.
Mueller Richard H.
Sedergran Thomas C.
Soundararajan Nachimuthu
E. R. Squibb & Sons Inc.
Owens Amelia
Park Ellen K.
Rotman Alan L.
LandOfFree
Process for the preparation of intermediates useful in the prepa does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of intermediates useful in the prepa, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of intermediates useful in the prepa will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1773298