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

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

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Extra resources for A critical review of the 1996 literature preceded by two chapters on current heterocyclic topics

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EtO)2POTMS N Et,3N,DMAP i i CO2-t-Bu 2. ,,~'-CO2CH2Ph AIBN, Benzene "N" I /~ CO2-t-Bu 96% 121 1. (CH3)3SiBr,Et3N 56% 2. H2, Pd/C 3. 4 Cyclizations at Phosphorus Glyphosate analogs formed through cyclizations at the phosphonate center are relatively rare in the chemical literature. The unusual oxazaphospholidine 124 has been isolated in high yield by carefully controlling the temperature below 60 ~ during the basic Mannich reaction with glycine described previously via intermediate 15 (72). As expected, acidic hydrolysis of 124 proceeded cleanly to produce GLYH3.

__ /~S~~ Br /~ 70% 129 OCH3 2. Et203PCI 65% 130 FI~ Et203Pf ~ S / " "~OCH3 1 31 ~ 10% HCI,THF H /~SL H203P 9 O _I. (CH3)aSiBr 2. H20 Acetone Et203P 3. Cyclohexyl amine 13 3 72~ H / O 132 was removed with tetrabutylammonium fluoride. Subsequent treatment with trimethylsilyl bromide and hydrolysis cleaved the phosphonate esters and produced the free phosphonic acid 136 in high yield. Removal of the N-benzyl protecting group was accomplished in good isolated yield by hydrogenolysis to give the desired 5-phosphono-l,2,4-triazol-3-one target 137.

Upon hydrolysis, and loss of CO2, 12 provided the related derivative, N-phosphonomethylethanolamine 13, which was oxidized at high temperature with a variety of metal catalysts including cadmium oxide (16) or Raney copper (17) to give GLYH3, after acidification. A similar oxidation route has also been reported starting from N-phosphonomethyl-morpholine (18). O ~1 ,~ (HO)2P'CH2N~ ? 12 H20, 200 oc -002 > O H (NO)2'I e l / ~ / / ~ / 770/0 OH 1. NaOH, CdO, H20, 225 ~ 2. b Mannich Reactions with Phosphite Esters under Neutral Conditions.

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