A Regioselective Approach to 5-Substituted-3-amino-1,2,4-triazines
Nucleophilic displacement of readily available α,α-dibromoketones with excess morpholine gave the corresponding ketoaminals, which upon condensation with aminoguanidine in MeOH in the presence of AcOH afforded 5-substituted-3-amino-1,2,4-triazines in >95% regioselectivity and 45−76% isolated yiel...
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| Published in | Organic letters Vol. 5; no. 13; pp. 2271 - 2274 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
26.06.2003
Amer Chemical Soc |
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| Abstract | Nucleophilic displacement of readily available α,α-dibromoketones with excess morpholine gave the corresponding ketoaminals, which upon condensation with aminoguanidine in MeOH in the presence of AcOH afforded 5-substituted-3-amino-1,2,4-triazines in >95% regioselectivity and 45−76% isolated yield. |
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| AbstractList | Nucleophilic displacement of readily available alpha,alpha-dibromoketones with excess morpholine gave the corresponding ketoaminals, which upon condensation with aminoguanidine in MeOH in the presence of AcOH afforded 5-substituted-3-amino-1,2,4-triazines in >95% regioselectivity and 45-76% isolated yield. [reaction: see text] Nucleophilic displacement of readily available α,α-dibromoketones with excess morpholine gave the corresponding ketoaminals, which upon condensation with aminoguanidine in MeOH in the presence of AcOH afforded 5-substituted-3-amino-1,2,4-triazines in >95% regioselectivity and 45−76% isolated yield. Nucleophilic displacement of readily available alpha,alpha-dibromoketones with excess morpholine gave the corresponding ketoaminals, which upon condensation with aminoguanidine in MeOH in the presence of AcOH afforded 5-substituted-3-amino-1,2,4-triazines in >95% regioselectivity and 45-76% isolated yield. Nucleophilic displacement of readily available alpha,alpha-dibromoketones with excess morpholine gave the corresponding ketoaminals, which upon condensation with aminoguanidine in MeOH in the presence of AcOH afforded 5-substituted-3-amino-1,2,4-triazines in >95% regioselectivity and 45-76% isolated yield. [reaction: see text] |
| Author | Devine, Paul N Limanto, John Volante, R. P Gauthier, Donald R Desmond, Richard A Reamer, Robert A |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/12816426$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1007_s00726_015_2135_6 crossref_primary_10_1021_jm301499r crossref_primary_10_1080_00397911_2014_891040 crossref_primary_10_1039_C5RA15919A crossref_primary_10_1021_cr300176g crossref_primary_10_1039_C7CC02078C crossref_primary_10_1016_j_tetlet_2009_01_021 crossref_primary_10_1039_c4gc00066h crossref_primary_10_2174_1570193X16666190724105040 crossref_primary_10_1021_jo0507035 crossref_primary_10_1055_a_1828_7504 crossref_primary_10_1255_ejms_1191 crossref_primary_10_1021_jm051200u crossref_primary_10_1021_acs_chemrev_1c00611 |
| Cites_doi | 10.1016/B978-008096518-5.00127-1 10.1021/jm00119a026 10.1016/S0040-4020(01)89544-2 10.1021/jo01293a022 10.1021/ja01340a042 10.1039/P19950001789 10.1002/jhet.5570190340 10.1021/jm00403a018 10.1021/jo00407a030 10.1002/jhet.5570310226 10.1002/jhet.5570230354 10.1248/yakushi1947.87.12_1501 |
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| Title | A Regioselective Approach to 5-Substituted-3-amino-1,2,4-triazines |
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