A critical review of the 1996 literature preceded by two by G.W. Gribble and T.L. Gilchrist (Eds.)

By G.W. Gribble and T.L. Gilchrist (Eds.)

Growth in Heterocyclic Chemistry (PHC) is an annual overview sequence commissioned through the overseas Society of Heterocyclic Chemistry (ISHC). The volumes within the sequence comprise either highlights of the former year's literature on heterocyclic chemistry and articles on new constructing subject matters of curiosity to heterocyclic chemists.

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Lee, L. ; Richard, T. J. S. Patent 4,810,426, 1989; to Monsanto. (a) Franczyk, T. S. S. Patent 5,292,936, 1994; to Monsanto. S. Patent 5,367,112,1994; to Monsanto. Miller, W. ; Neumann, T. E. S. Patent 4,587,061, 1986; to Monsanto. ; Nagy, L. T. S. Patent 4,065,491, 1977; to Chinoin. , CA 109:73659a. Graziello, D. a. Brendel, M. ; Szentiralyi, I. ; Bite, E. ; Repasi, J. S. Patent 4,486,359, 1984; to Alkaloida. Ehrat, R. S. Patent 4,237,065, 1980; to Biological Chemical Activities. Natehev, I.

The synthesis of 5-phosphonothiazolin-2-one 133 started with 2-bromothiazole 129. Nucleophilic displacement of the 2-bromide proceeded cleanly with hot anhydrous sodium methoxide to give 2-methoxythiazole 130. Low-temperature metalation of 130 with n-butyl lithium occurred selectively at the 5-position (76), and subsequent electrophilic trapping with diethyl chlorophosphate produced the 5-phosphonate 131. Deprotection of 131 was accomplished either stepwise with mild acid to produce the thiazolin-2-one intermediate 132, or directly with trimethylsilyl bromide to give the free phosphonic acid 133, which was isolated as its cyclohexylammonium salt.

T(CH3)3SiO]3P N'COSEt 34 O CH3CN,25 ~ 2. i-PrOH,H20 55-70% H 35 Examples of cyclic aliphatic or aryl phosphonate uiesters, such as 36 or 37 have also been prepared by this HHT method from their cyclic phosphite precursors (2). O ~-'O H o/P 36 N 37 CO2R Another interesting application utilized an analogous ring-opening reaction between phosphites and a benzoxazine 38 to produce a protected N-benzyl-glyphosate derivative 39 directly. Hydrogenolysis and saponification then gave GLYNa3. These benzoxazines were readily prepared from a base-catalyzed reaction between p-cresol, formaldehyde, and either ethyl or sodium glycinate (47).

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