Ring Enlargement of N‑Phosphanyl-1,2,3,4-tetrahydroquinazolines

We found that 1-phosphanyl-1,2,3,4-tetrahydroquinazolines undergo ring enlargement. Their treatment with trifluoroacetic or hydrochloric acid afforded diazaphosphepinium salts. Deprotonation of these salts gave the corresponding neutral diazaphosphepines. The reaction of 1-phosphanyl-1,2,3,4-tetrahy...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-11, Vol.85 (22), p.14467-14472
Main Authors: Marchenko, Anatoliy, Koidan, Georgyi, Hurieva, Anastasiia N, Shishkina, Svitlana, Rusanov, Eduard, Kostyuk, Aleksandr
Format: Article
Language:English
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Summary:We found that 1-phosphanyl-1,2,3,4-tetrahydroquinazolines undergo ring enlargement. Their treatment with trifluoroacetic or hydrochloric acid afforded diazaphosphepinium salts. Deprotonation of these salts gave the corresponding neutral diazaphosphepines. The reaction of 1-phosphanyl-1,2,3,4-tetrahydroquinazolines with diazomethane or phenylazide afforded triazaphosphocine derivatives via insertion of P–N moiety. At the same time, an analogous hexahydropyrimidine derivative reacted with phenylazide in a normal manner at the phosphorus atom to afford the P­(V) derivative.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00750