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Synthesis and Transformations of Urazoles Derived from 7,7‐Dicarboxynorcaradiene: Formation of 2,4‐Dioxohexahydro‐1,3,5‐Triazines by an Unusual Base‐Catalyzed Rearrangement by Waldemar Adam; Sven Grabowski; Ricardo F. Hinz; Vittorio Lucchini; Eva‐Maria Peters; Karl Peters; Hector Rebollo; Hans Georg von Schnering is a Chemistry article available to read on EtoBox.
What is Synthesis and Transformations of Urazoles Derived from 7,7‐Dicarboxynorcaradiene: Formation of 2,4‐Dioxohexahydro‐1,3,5‐Triazines by an Unusual Base‐Catalyzed Rearrangement about?
4-Phenyl-l.2,4-triazolinc-3.5-dione (PTAD) or 4-mcthyl-l.2.4-triazolinc-3,5-dione (MTAD) cycloaddition to the 7-cyclohcptatrienecarboxylates gave the endo-urazolcs I . With the 7.7-cyclohcptatrienedicarboxylatcs 5 the urazoles 6 were formed. Dccarboxylation of urazole 6 c led to c,rtdo-l b, showing that steric factors prevcnt formation of the desired exo-1 b isomer. Attempts to isornerize undo-l b and rndo-1 c by base catalysis, afforded after methylation with mcthyl iodide the 2,4-dioxohcxahydro-1,3,5-triazine derivativcs 2a,b. This unusual rcarrangcmcnt also took placc with urazolc 3 leading to 1,3.5-triazine 4. but the urazolcs derived from butadicne and cyclopntadiene did not respond. ' H NMR diffcrentid NOE and X-ray analysis of 2b and 6c were necessary for the structural elucid:rtion of the 1.3.5-triazines 2a, b.
Who reads Synthesis and Transformations of Urazoles Derived from 7,7‐Dicarboxynorcaradiene: Formation of 2,4‐Dioxohexahydro‐1,3,5‐Triazines by an Unusual Base‐Catalyzed Rearrangement?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Waldemar Adam; Sven Grabowski; Ricardo F. Hinz; Vittorio Lucchini; Eva‐Maria Peters; Karl Peters; Hector Rebollo; Hans Georg von Schnering
- Publisher
- Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0009-2940)
- Published
- 1987
- Language
- EN
- Field
- Chemistry (Physical Sciences)