Synthesis of 2-Amino-4-pyrimidinones from Resin-Bound Guanidines Prepared Using Bis(allyloxycarbonyl)-Protected Triflylguanidine
We have synthesized novel heterocyclic compounds from resin-bound guanidines. For this purpose, an amine immobilized on a solid support was acylated with protected amino acids. Following the deprotection, the liberated amines were guanidinylated utilizing a new member of the family of diurethane-pro...
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| Veröffentlicht in: | Journal of organic chemistry 2003-12, Vol.68 (26), p.10092-10097 |
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| container_end_page | 10097 |
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| container_issue | 26 |
| container_start_page | 10092 |
| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Zapf, Christoph W Goodman, Murray |
| description | We have synthesized novel heterocyclic compounds from resin-bound guanidines. For this purpose, an amine immobilized on a solid support was acylated with protected amino acids. Following the deprotection, the liberated amines were guanidinylated utilizing a new member of the family of diurethane-protected triflyl guanidine reagents, N,N‘-bis(allyloxycarbonyl)-N‘ ‘-triflylguanidine. The deprotected guanidines were subsequently regioselectively cyclized with β-keto esters yielding novel compounds containing heterocyclic structures in high purities. |
| doi_str_mv | 10.1021/jo035201a |
| format | Article |
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Org. Chem</addtitle><description>We have synthesized novel heterocyclic compounds from resin-bound guanidines. For this purpose, an amine immobilized on a solid support was acylated with protected amino acids. Following the deprotection, the liberated amines were guanidinylated utilizing a new member of the family of diurethane-protected triflyl guanidine reagents, N,N‘-bis(allyloxycarbonyl)-N‘ ‘-triflylguanidine. 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Org. Chem</addtitle><date>2003-12-26</date><risdate>2003</risdate><volume>68</volume><issue>26</issue><spage>10092</spage><epage>10097</epage><pages>10092-10097</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>We have synthesized novel heterocyclic compounds from resin-bound guanidines. For this purpose, an amine immobilized on a solid support was acylated with protected amino acids. Following the deprotection, the liberated amines were guanidinylated utilizing a new member of the family of diurethane-protected triflyl guanidine reagents, N,N‘-bis(allyloxycarbonyl)-N‘ ‘-triflylguanidine. The deprotected guanidines were subsequently regioselectively cyclized with β-keto esters yielding novel compounds containing heterocyclic structures in high purities.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14682705</pmid><doi>10.1021/jo035201a</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2003-12, Vol.68 (26), p.10092-10097 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Amines - chemistry Amino Acids - chemistry Chemistry Cyclization Esters - chemistry Exact sciences and technology Guanidines - chemistry Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties Pyrimidinones - chemical synthesis Pyrimidinones - chemistry Resins, Synthetic - chemistry Solvents - chemistry Stereoisomerism |
| title | Synthesis of 2-Amino-4-pyrimidinones from Resin-Bound Guanidines Prepared Using Bis(allyloxycarbonyl)-Protected Triflylguanidine |
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