Regular Issue

Vol. 22, No. 2, 1984

32 data found. 31 - 32 listedFirst Previous
Report | Regular issue | Vol 22, No. 2, 1984, pp. 379 - 386
Published online:
DOI: 10.3987/R-1984-02-0379
On the Reaction of Indole with Sodium Borohydride in Triflueoacetatic Acid

Gordon W. Gribble,* Charles F. Nutaitis, and Robert M. Leese

*Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03775, U.S.A.
only F-trifluoroethylat~on.


The reaction of indole (1) with sodium borohydride in trifluoroacetic acid gives, successively, indoline (3), N-(2,2,2-trifluoroethyl)indoline (4), and 1,1,1-trifluoro-2, 2-bis[5- (N-(2,2,2-trifluoroethyl)indolinyl]ethane (5), whose structure is established by chemical and spectral means. Similar reactions are observed with N-methylaniline (8) and anisole, but not with dibenzazepines 13 and 15, which give only N-trifluoroethylation.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 387 - 390
Published online:
DOI: 10.3987/R-1984-02-0387
Reaction of Haloacetoacetate with L-Cysteine Ethyl Ester —Synthesis of 1,4-thiazine Derivatives

Takuo Chiba,* Hirotoshi Sato, Teiko Kayaba, and Tetsuzo Kato

*Faculty of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, sendai 980-8578, Japan
tetrahydro-2H-l,4-thiazine (s) in 62% yield. Reaction of 4-


Reaction of ethyl 2-chloroacetoacetate (2a) L-cysteine ethyl ester (1) gave 3,6-diethoxycarbonyl-5-methyl-3,4-dihydro-2H-1,4-thiazine (3a). Similarly, 2-chloroacetoacetanilides 2b-2d reacted with 1 to give 6-carbamoyl-5-methyl-3,4-dihydro-2H-l,4-thiazines 3b-3d. Ethyl 4-bromoacetoacetate (4a) reacted with L-cysteine ethyl ester (1) to give 3-ethoxycarbonyl-5-(ethoxycarbonylmethylene)tetrahydro-2H-l,4-thiazine (5a) in 62% yield. Reaction of 4-bromoacetoacetanilides 4b and 4c with 1 gave 5-(carbamoylmethylene)tetrahydro-2H-1,4-thiazines 5b and 5c, respectively.

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32 data found. 31 - 32 listedFirst Previous