- Modular synthesis of 3,6-disubstituted-1,2,4-triazines via the cyclodehydration of β-keto- N -acylsulfonamides with hydrazine salts
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A straightforward method for preparing 3,6-disubstituted-1,2,4-triazines through a redox-efficient cyclodehydration of β-keto-N-acylsulfonamides with hydrazine salts is described. Two approaches for synthesizing the requisite β-keto-N-acylsulfonamides are presented, which allow for the late stage incorporation of either the C3 or C6 substituent in a flexible manner from acid chlorides or α-bromoketones, respectively. The scope of this methodology includes primary and secondary sp3-linked substituents at both the C3 and C6 positions, and the mild reaction conditions tolerate a variety of sensitive functionalities.
- Dowling, Matthew S.,Jiao, Wenhua,Hou, Jie,Jiang, Yuchun,Gong, Shangsheng
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- Zn-catalyzed hydrohydrazination of propargylamides with BocNHNH2: A novel entry into the 1,2,4-triazine core
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Hydrohydrazination of a variety of propargylamides with BocNHNH2 under Zn(OTf)2 catalysis, unexpectedly, gave dihydro-1,2,4-triazines with a loss of the protecting group. The initial products can be efficiently aromatized in situ wit
- Lukin, Alexey,Vedekhina, Tatiana,Tovpeko, Dmitry,Zhurilo, Nikolay,Krasavin, Mikhail
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p. 57956 - 57959
(2016/07/07)
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- STUDIES ON AS-TRIAZINE DERIVATIVES. IX. SYNTHESIS OF 5-SUBSTITUTED 1,2,4-TRIAZINE DERIVATIVES THROUGH AN ADDITION REACTION AND SUBSEQUENT OXIDATION
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The addition reactions of various nucleophiles to 6-methyl-3-phenyl-1,2,4-triazine (1) were investigated and a practical preparation of 1 was developed.The reactions showed many similarities to those of quinazoline (at the 4-position) and acridine (at the
- Konno, Shoetsu,Ohba, Setsuya,Sagi, Mataichi,Yamanaka, Hiroshi
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p. 1378 - 1382
(2007/10/02)
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- STUDIES ON as-TRIAZINE DERIVATIVES. VII. RESEMBLANCE BETWEEN as-TRIAZINES AND QUINAZOLINES IN NUCLEOPHILIC ADDITION-ELIMINATION REACTIONS.
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Alike 4-chloroquinazoline, 5-chloro-1,2,4-triazines (as-triazines) reacted with aromatic aldehydes in the presence of 1,3-dimethylbenzimidazolium iodide under basic conditions to give 5-aroyl-as-triazines.The Grignard reaction of 5-cyano-as-triazine with arylmagnesium bromides failed to give any significant product.Some analogy of as-triazines with quinazolines, in their chemical properties, was additionally investigated.
- Konno, Shoetsu,Ohba, Setsuya,Sagi, Mataichi,Yamanaka, Hiroshi
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p. 1243 - 1246
(2007/10/02)
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