Synthesis of new pyrido[2,3-d]pyrimidin-5-one, pyrido[2,3-d]pyrimidin-7-one, and pyrimidino[4,5-d][1,3]oxazine derivatives from 5-acetyl-4-aminopyrimidines
Methods were developed for the synthesis of new pyrido[2,3- d ]pyrimidine and pyrimidino[4,5- d ][1,3]oxazine derivatives. When heated under reflux with MeONa in BuOH, 5-acetyl-4-aminopyrimidines, acylated with carboxylic anhydrides or acid chlorides, are transformed into pyrido[2,3- d ]pyrimidin-5-...
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| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2021-08, Vol.57 (7-8), p.787-798 |
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| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 57 |
| creator | Komkov, Alexander V. Kozlov, Mikhail A. Dmitrenok, Andrey S. Kolotyrkina, Nataliya G. Minyaev, Mikhail E. Zavarzin, Igor V. |
| description | Methods were developed for the synthesis of new pyrido[2,3-
d
]pyrimidine and pyrimidino[4,5-
d
][1,3]oxazine derivatives. When heated under reflux with MeONa in BuOH, 5-acetyl-4-aminopyrimidines, acylated with carboxylic anhydrides or acid chlorides, are transformed into pyrido[2,3-
d
]pyrimidin-5-one derivatives, i.e., the acetyl methyl group and the amide carbonyl moiety are involved in the cyclization. In the presence of an activated CH
2
group (e.g
.
, PhCH
2
) in the amide moiety, the cyclization involves this group and the acetyl carbonyl giving rise to pyrido[2,3-
d
]pyrimidin-7-one derivatives. The reaction of 5-acetyl-4-aminopyrimidines with carboxylic acid chlorides under reflux in xylene followed by addition of a base affords pyrimidino[4,5-
d
][1,3]oxazines. |
| doi_str_mv | 10.1007/s10593-021-02982-8 |
| format | Article |
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d
]pyrimidine and pyrimidino[4,5-
d
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d
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2
group (e.g
.
, PhCH
2
) in the amide moiety, the cyclization involves this group and the acetyl carbonyl giving rise to pyrido[2,3-
d
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d
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d
]pyrimidine and pyrimidino[4,5-
d
][1,3]oxazine derivatives. When heated under reflux with MeONa in BuOH, 5-acetyl-4-aminopyrimidines, acylated with carboxylic anhydrides or acid chlorides, are transformed into pyrido[2,3-
d
]pyrimidin-5-one derivatives, i.e., the acetyl methyl group and the amide carbonyl moiety are involved in the cyclization. In the presence of an activated CH
2
group (e.g
.
, PhCH
2
) in the amide moiety, the cyclization involves this group and the acetyl carbonyl giving rise to pyrido[2,3-
d
]pyrimidin-7-one derivatives. The reaction of 5-acetyl-4-aminopyrimidines with carboxylic acid chlorides under reflux in xylene followed by addition of a base affords pyrimidino[4,5-
d
][1,3]oxazines.</description><subject>Carbonyls</subject><subject>Carboxylic acids</subject><subject>Chemical properties</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chlorides</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Pyrimidines</subject><subject>Synthesis</subject><subject>Xylene</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kd9qXCEQxiWk0E3aF-jVgd6uqY7HVS9DSNNCoBdtr5Ygs0dNDLu61ZM_21fJy8btKclVi4jMzPebcfgI-cDZCWdMfaqcSSMoA96u0UD1AZlxqQTVQopDMmOMGSo4wFtyVOttCxXX_Yw8fd-l8cbXWLscuuQfuu2uRJeXMBfUXe2DTXQxUUlz8vN_VdVUxeS6l2Re9nPZVEs-F1f5EX_H5DvnS7zHMd772oWSN52kOPhxt6Y9xU2DXnBf35E3AdfVv__7HpOfn89_nH2hl98uvp6dXtJBSD1SgwvXO8GxN1I6NFoAmsBWAaFXbgWoxUqqBQgcelgwDMGARANMr7wenBLH5OPUd1vyrztfR3ub70pqIy1IpXojAHRTnUyqa1x7G1PIY8GhHec3cWjrh9jypwulAAQzvAEwAUPJtRYf7LathmVnObN71-zkmm2u2T-u2f0UMUG1idO1L69_-Q_1DCgOmwA</recordid><startdate>20210801</startdate><enddate>20210801</enddate><creator>Komkov, Alexander V.</creator><creator>Kozlov, Mikhail A.</creator><creator>Dmitrenok, Andrey S.</creator><creator>Kolotyrkina, Nataliya G.</creator><creator>Minyaev, Mikhail E.</creator><creator>Zavarzin, Igor V.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20210801</creationdate><title>Synthesis of new pyrido[2,3-d]pyrimidin-5-one, pyrido[2,3-d]pyrimidin-7-one, and pyrimidino[4,5-d][1,3]oxazine derivatives from 5-acetyl-4-aminopyrimidines</title><author>Komkov, Alexander V. ; Kozlov, Mikhail A. ; Dmitrenok, Andrey S. ; Kolotyrkina, Nataliya G. ; Minyaev, Mikhail E. ; Zavarzin, Igor V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-9a6d4d31a4955da9832a9f0bfa247db2a83b57623ac4260aff925a9208be8cd73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Carbonyls</topic><topic>Carboxylic acids</topic><topic>Chemical properties</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chlorides</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Pyrimidines</topic><topic>Synthesis</topic><topic>Xylene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Komkov, Alexander V.</creatorcontrib><creatorcontrib>Kozlov, Mikhail A.</creatorcontrib><creatorcontrib>Dmitrenok, Andrey S.</creatorcontrib><creatorcontrib>Kolotyrkina, Nataliya G.</creatorcontrib><creatorcontrib>Minyaev, Mikhail E.</creatorcontrib><creatorcontrib>Zavarzin, Igor V.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Komkov, Alexander V.</au><au>Kozlov, Mikhail A.</au><au>Dmitrenok, Andrey S.</au><au>Kolotyrkina, Nataliya G.</au><au>Minyaev, Mikhail E.</au><au>Zavarzin, Igor V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of new pyrido[2,3-d]pyrimidin-5-one, pyrido[2,3-d]pyrimidin-7-one, and pyrimidino[4,5-d][1,3]oxazine derivatives from 5-acetyl-4-aminopyrimidines</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2021-08-01</date><risdate>2021</risdate><volume>57</volume><issue>7-8</issue><spage>787</spage><epage>798</epage><pages>787-798</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>Methods were developed for the synthesis of new pyrido[2,3-
d
]pyrimidine and pyrimidino[4,5-
d
][1,3]oxazine derivatives. When heated under reflux with MeONa in BuOH, 5-acetyl-4-aminopyrimidines, acylated with carboxylic anhydrides or acid chlorides, are transformed into pyrido[2,3-
d
]pyrimidin-5-one derivatives, i.e., the acetyl methyl group and the amide carbonyl moiety are involved in the cyclization. In the presence of an activated CH
2
group (e.g
.
, PhCH
2
) in the amide moiety, the cyclization involves this group and the acetyl carbonyl giving rise to pyrido[2,3-
d
]pyrimidin-7-one derivatives. The reaction of 5-acetyl-4-aminopyrimidines with carboxylic acid chlorides under reflux in xylene followed by addition of a base affords pyrimidino[4,5-
d
][1,3]oxazines.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-021-02982-8</doi><tpages>12</tpages></addata></record> |
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| ispartof | Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2021-08, Vol.57 (7-8), p.787-798 |
| issn | 0009-3122 1573-8353 |
| language | eng |
| recordid | cdi_proquest_journals_2577493228 |
| source | SpringerNature Journals |
| subjects | Carbonyls Carboxylic acids Chemical properties Chemistry Chemistry and Materials Science Chlorides Organic Chemistry Pharmacy Pyrimidines Synthesis Xylene |
| title | Synthesis of new pyrido[2,3-d]pyrimidin-5-one, pyrido[2,3-d]pyrimidin-7-one, and pyrimidino[4,5-d][1,3]oxazine derivatives from 5-acetyl-4-aminopyrimidines |
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