Synthesis of Thiazolium Substituted gem-Bisphosphonates and Investigation of Some their Properties
In the course of our investigation on aminobisphosphonic acids we have developed the synthesis of thioureidoalkylidene- (11) and aminothiazole-I .I-bisphosphonic acids (III, IV): We have established that thioureas (11) by the reaction of Hantzsch with a-bro-moketones yielded the thiazolium substitut...
Saved in:
Published in | Phosphorus, sulfur, and silicon and the related elements Vol. 147; no. 1; p. 241 |
---|---|
Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
Taylor & Francis Group
01.01.1999
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | In the course of our investigation on aminobisphosphonic acids we have developed the synthesis of thioureidoalkylidene- (11) and aminothiazole-I .I-bisphosphonic acids (III, IV):
We have established that thioureas (11) by the reaction of Hantzsch with a-bro-moketones yielded the thiazolium substituted bisphosphonates (Ill) or (IV) depending on the nature of the substituents R and the steric hindiance. As a rule only less hindered nitrogen atom is involved into the cyclization with formation of one from two of possible isomers. Compounds (IV) are formed if R=Ar and n>O. Compounds (III) are formed if R=R
3
CH
2
and n=O. In the case when R=Ar and n=O mixture of both (III) and (IV) forms. Reaction of sterically hindered thioureas (II)with n=O and R=Adamantyl- or ferf-Bu- with bromoacetone leads to thiazole (III)also. But reactions with bromoacetophenones stop before dehydratation step on thiazolines in these cases. |
---|---|
ISSN: | 1042-6507 1563-5325 |
DOI: | 10.1080/10426509908053601 |