Application of the tisler triazolopyrimidine cyclization to the synthesis of a crop protection agent and an intermediate

Organic Process Research and Development

Volumn 10, Issue 6, 2006, Pages 1167-1171

  Bell, Bruce M ^a   Fanwick, Phillip E ^b   Graupner, Paul R ^c   Roth, Gary A ^a  

^a DOW CHEMICAL COMPANY   (United States)

^b PURDUE UNIVERSITY   (United States)

^c DOW AGROSCIENCES LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845496313     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0601518     Document Type: Article

References (13)

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3. Ringer, J. W.; Pearson, D. L.; Scott, C. A.; Wallin, A. P. N-Arylsufilimine Compounds and Their Use as Catalysts in the Preparation of N-Arylarylsulfonamide Compounds. U.S. Patent 6.114,580, September 5, 2000.
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5. For an earlier preparation of 3, see: Bee, M. A.; Rose, F. J. Chem. Soc. C 1966, 2031.
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7. Diehr, H. J.; Pest, C.; Kirsten, R.; Kluth, J.; Mueller, K. H.; Pfister, T.; Priesnitz, U.; Rieble, H. J.; Roy, W. EP 173321, 1986.
8. D'Alo, G.; Perghum, M.; Grunanger, P. Ann. Chim. (Rome) 1963, 53, 1405-1410;
9. Gross, M.; Held, P.; Schubert, H. J. Prakt Chem. 1974, 316, 434.
10. The intermediate S-methylisothiourea 15 could be isolated: however, it was more convenient to use the acetonitrile solution of the intermediate in the following step.
11. Riedel, H. J. EP 533012, 1993; CAN 119:72622.
12. Gesing, E. R.; Fest, C.; Kirsten, R.; Kluth, J.; Mueller, K. H.; Helmut, K.; Riebel, H. J.; Santel, H. J.; Luerssen, K. S.; Rober, T. EP 413221, 1991: CAN: 115:87494.
13. 15N see: Martin, G. E.; Hadden, C. E. J. Nat. Prod. 2000, 63, 543.