Mannich-Type Reaction for Synthesis of 3-Methyl-4-nitroimino-tetrahydro-1,3,5-oxadiazine

REFERENCES

• Wan , D. Z. Mannich Reaction and Mannich Base Chemistry ; Science Press : Beijing , 1986 .
   Google Scholar
• Wang , S. Y. ; Cao , D. ; Huang , L. R. Application of Mannich reaction in drug synthesis . Hebei J. Ind. Sci. Tech. 2006 , 23 , 44 – 47 .
   Google Scholar
• Thompson , B. B. The Mannich reaction: Mechanistic and technological considerations . J. Pharm. Sci. 1968 , 57 , 715 – 733 .
   PubMed Web of Science ®Google Scholar
• Benkovic , S. J. ; Benkovic , P. A. ; Comfort , D. R. Kinetic detection of the imminium cation in formaldehyde–amine condensations in neutral aqueous solution . J. Am. Chem. Soc. 1969 , 91 , 1860 – 1861 .
   Web of Science ®Google Scholar
• Mannich , C. Synthesis of β-ketonic bases . J. Chem. Soc., Abstr. 1917 , 112 , 634 – 635 .
   Google Scholar
• Mannich , C. Mannich reaction . Arch. Pharm. 1912 , 250 , 647 .
   Google Scholar
• Maienfisch , P. Synthesis and properties of thiamenthoxam and related compounds . Z. Naturforsch. B: Chem. Sci. 2006 , 61 , 353 – 359 .
   Google Scholar
• Maienfisch , P. ; Haettenschwiler , J. ; Rindlisbacher , A. ; Decock , A. ; Wellmann , H. ; Kayser , H. Azido-neonicotinoids as candidate photoaffinity probes for insect nicotinic acetylcholine receptors . Chimia 2003 , 57 , 710 – 714 .
   Web of Science ®Google Scholar
• Maienfisch , P. ; Gsell , L. ; Rindlisbacher , A. Synthesis and insecticidal activity of CGA 293′343, a novel broad-spectrum insecticide . Pestic. Sci. 1999 , 55 , 351 – 355 .
   Google Scholar
• Gobel , T. ; Gsell , L. ; Huter , O. F. ; Maienfisch , P. ; Naef , R. ; O'Sullivan , A. C. ; Pitterna , T. ; Rapold , T. ; Seifert , G. ; Senn , M. ; Szczepanski , H. ; Wadsworth , D. J. Synthetic approaches towards CGA 293′343, a novel broad-spectrum insecticide . Pestic. Sci. 1999 , 55 , 355 – 357 .
   Google Scholar
• Fan , W. Z. ; Cheng , Z. M. ; Gu , B. Q. ; Zhang , Y. B. Research on synthetic methods of thiamethoxam . Shanghai Chem. Indust. 2002 , 27 , 25 – 27 .
   Google Scholar
• Kang , T. N. ; Ling , Y. ; She , Y. H. ; Chen , F. H. ; Yang , X. L. Synthesis of 3-acetyl-4-nitroimino-perhydro-1,3,5-oxadiazine as an intermediate for new nicotinyl pesticides . Chin. J. Pestic. 2005 , 44 , 108 – 109 .
   Google Scholar
• Zhou , T. ; Chen , S. T. ; Chen , Z. W. Reviews on synthetic methods of thiamethoxam. Zhejiang Chem. Indust. 2006, 37, 24–26.
   Google Scholar
• Tao , X. J. ; Huang , C. Q. ; Luo , L. M. Research on synthesis methods of thiamethoxam . Mod. Agrochem. 2006 , 5 , 11 – 13 .
   Google Scholar
• Yang , H. ; Wu , G. X. ; Zhang , Z. M. ; Gao , S. ; Feng , R. ; Liang , M. ; Sun , K. Synthesis of 3-methyl-4-nitroiminoperhydro-1,3,5-oxadiazine . Chin. J. Pestic. 2006 , 45 , 24 – 26 .
   Google Scholar
• Metelkina , E. L. 2-Nitroguanidine derivatives, X: Synthesis and nitration of 4-nitriminotetrahydro-1,3,5-oxadiazine and 2-nitriminohexahydro-1,3,5-triazine and their substituted derivatives . Russ. J. Org. Chem. 2007 , 43 , 1437 – 1440 .
   Web of Science ®Google Scholar
• Maienfisch , P. ; Huerlimann , H. ; Haettenschwiler , J. A novel method for the preparation of N,N′-disubstituted-N″-nitroguanidines, including a practical synthesis of the neonicotinoid insecticide clothianidin . Tetrahedron Lett. 2000 , 41 , 7187 – 7191 .
   Web of Science ®Google Scholar
• Bur , S. K. ; Martin , S. F. Vinylogous Mannich reactions: Stereoselectivity and synthetic utility . Tetrahedron 2001 , 57 , 3221 – 3242 .
   Web of Science ®Google Scholar
• List , B. The direct catalytic asymmetric three-component Mannich reaction . J. Am. Chem. Soc. 2000 , 122 , 9336 – 9337 .
   Web of Science ®Google Scholar
• Cha , Z. M. ; Lv , G. H. Preparation of N-methyl-N′-nitroguanidin. CN Patent 101066939 A, 2007 .
   Google Scholar
• Bayer , A. G. Verfahren zur herstellung von N-methyl-N′-nitroguanidin. EP Patent 0798293A1, 1997 .
   Google Scholar
• Maienfisch , P. ; Huerlimann , H. ; Rindlisbacher , A. ; Gsell , L. ; Dettwiler , H. ; Haettenschwiler , J. ; Sieger , E. ; Walti , M. The discovery of thiamethoxam: A second-generation neonicotinoid . Pest. Manag. Sci. 2001 , 57 , 165 – 176 .
   PubMed Web of Science ®Google Scholar
• Wang , D. S. ; Yang , X. L. ; Han , B. Synthesis of 1-methyl-2-nitroimino-5- methyl-1,3,5-triazacyclohexane . Chem. Engin. 2009 , 12 , 10 – 11 .
   Google Scholar
• Maienfisch , P. ; Kristiansen , O. ; Gsell , L. Triazacyclohexanderivate. EP Patent 0483055A1, 1992 .
   Google Scholar
• Liu , A. C. ; Zhang , L. ; Tan , Z. Y. ; Liu , F. Study of synthetic process of novel neonicotinoid dinotefuran . World Pesticides 2009 , 31 , 22 – 23 .
   Google Scholar
• Odaka , K. ; Kinoshita , K. ; Wakita , T. ; Shiraishi , S. ; Oonuma , K. Preparation of 1-(tetrahydro-3-furanylmethyl)-2-(nitroimino)-1,3,5-triazine derivatives as insecticides and method for production thereof. JP Patent 07173157A, 1995 .
   Google Scholar
• Maienfisch , P. ; Kristiansen , O. ; Gsell , L. Process for the preparation of nitroguanidine derivatives. EP Patent 0483062A2, 1995 .
   Google Scholar