- Synthesis of Soai Type 2-Arylpyrimidine-5-carbaldehydes through Desulfurative Cross-Coupling with Arylboronic Acids
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A two-step synthesis of 2-arylpyrimidine-5-carbaldehydes, which are of relevance as substrates for Soai's asymmetric autocatalysis, was realized by exploiting a hidden threefold symmetry in the target core structure. Condensation of Arnold's C 3-symmetric vinamidinium cation with S-methylisothiouronium sulfate provides 2-methylsulfanyl-pyrimidine-5-carbaldehyde; introduction of aryl groups at C-2 of the latter was accomplished by a Liebeskind-Srogl palladium-catalyzed desulfurative (de-methylsulfanylative) coupling with aryl boronic acids to obtain the target compounds 1 (14 examples, 60-95 % yield). 2-Arylpyrimidine-5-carbaldehydes, which are of relevance as substrates in Soai's asymmetric autocatalysis, are prepared through Liebeskind-Srogl coupling of aryl boronic acids with 2-methylthiopyrimidine-5-carbaldehyde; the latter is obtained in a hydrolytic condensation of two symmetric amidinium salts.
- Maltsev, Oleg V.,Rausch, Rodger,Quan, Zheng-Jun,Hintermann, Lukas
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supporting information
p. 7426 - 7432
(2016/02/20)
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- Formation of Pyrimidine-5-carboxaldehydes, 1-Aminoethylene-2,2-dicarboxaldehyde and 2-Amino-4-anilino-1,3,5-triazine from Triformylmethane and Amidines
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Triformylmethane (1) reacted with benzamidine, guanidine and S-methylisothiourea to give the corresponding 2-substituted pyrimidines-5-carboxaldehydes.However reactions of 1 with acetamidine (or formamidine) and phenylbiguanide gave the unexpected 1-aminoethylene-2,2-dicarboxaldehyde (5) and 2-amino-4-anilino-1,3,5-triazine (9), respectively.
- Takagi, Kaname,Bajnati, Abdelilah,Hubert-Habart, Michel
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p. 973 - 976
(2007/10/02)
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- DIRECT SYNTHESIS OF 2-SUBSTITUTED 5-FORMYLPYRIMIDINES AND RING TRANSFORMATION OF THEIR PHENYLHYDRAZONES INTO 4-FORMYL-1-PHENYLPYRAZOLE
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Triformylmethane (1) reacted with benzamidine, guanidine and S-methylisothiourea to give 2-substituted 5-formylpyrimidines (2a-c), whose phenylhydrazones (3a-c) readily underwent ring transformation into 4-formyl-1-phenylpyrazole (4) on heating in acidic methanol.
- Takagi, Kaname,Bajnati, Abdelilah,Hubert-Habart, Michel
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p. 1105 - 1109
(2007/10/02)
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- Direct syntheses of pyrazole-4-carbaldehydes and pyrimidine-5-carbaldehydes starting from triformylmethane.
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Triformylmethane is transformed into the pyrazole-4-carbaldehydes 2, 4, 6, 7, 9, 11 and the pyrazole-4-carbaldehydes 8, 10, 12 by corresponding hydrazines, and into the pyrimidine-5-carbaldehydes 13, 14, 15 by appropriate amidines.
- Takagi, K.,Bajnati, A.,Hubert-Habart, M.
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p. 660 - 666
(2007/10/02)
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