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Synthesis of the Spiro Derivatives of 1,2-Oxaphosphetes by [2+2] Cycloaddition of Cyclic 1-(2,4,6-Triisopropylphenyl)phosphine Oxides with Dimethyl Acetylenedicarboxylate

✍ Scribed by György Keglevich; Henrietta Forintos; György Miklós Keserű; László Hegedűs; László Tőke

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
134 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐMembers of a new heterocyclic family, 1,2-oxaphosphetes were prepared by the unexpected [212] cycloaddition of the PvO group of 1-(2,4,6-triisopropylphenyl) P-heterocycles with the acetylene moiety of dimethyl acetylenedicarboxylate. The new oxaphosphetes are spiro derivatives of the starting heterocycles and exhibit a phosphorus atom with trigonal bipyramidal geometry. PM3 semiempirical calculations justi®ed the novel reaction path and suggested a stepwise reaction mechanism.

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The reaction of isoquinoline and dimethy
The reaction of isoquinoline and dimethyl acetylenedicarboxylate with 1,2- and 1,4-benzoquinones: a novel synthesis of spiro[1,3]oxazino[2,3-a]isoquinolines
✍ Vijay Nair; A.R Sreekanth; A.T Biju; Nigam P Rath 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 221 KB

The 1,4-dipolar intermediate generated by the addition of isoquinoline to dimethyl acetylenedicarboxylate is trapped by 1,2-and 1,4-benzoquinones to afford spiro[1,3]oxazino[2,3-a]isoquinoline derivatives in high yields.