70326-72-6Relevant academic research and scientific papers
Synthesis of highly substituted pyrimidine fused uracils by PhI(OAc)2/TEMPO-catalyzed oxidative insertion of alcohols into N-uracil amidines
Debnath, Pradip
, (2022/01/20)
An efficient and sustainable organocatalyst-catalyzed protocol for the synthesis of structurally diverse pyrimidine fused uracils via the oxidative insertion of alcohols into N-uracil amidines has been developed. With 1.2 equiv. of PhI(OAc)2 in combination with 10 mol% of TEMPO as the catalyst and Cs2CO3 as the base, this protocol has been applied to synthesize a small library of pyrimidine fused uracils in high yields. The PhI(OAc)2/TEMPO-catalyzed oxidation of alcohol in-situ generated an aldehyde intermediate, which is subsequently reacted with N-uracil amidine to provide the highly functionalized pyrimidine fused uracils. The protocol is operationally simple, and applicable to a broad range of alcoholic substrates, making it highly practical approach for the preparation of pyrimidine fused uracils of biological significance.
Synthesis of functionalized pyrimidouracils by ruthenium-catalyzed oxidative insertion of (hetero)aryl methanols into N-uracil amidines
Debnath, Pradip,Sahu, Gouranga,De, Utpal C.
, (2020/12/01)
A dehydrogenative coupling of N-uracil amidines with (hetero)aryl methanols has been developed, allowing for the facile synthesis of a broad range of structurally diverse pyrimidouracils. By applying [RuCl2(p-cymene)]2/Cs2CO3 as an efficient catalytic system, the easily available, cheap (hetero)aryl methanols were firstly employed for oxidative insertion/C-H amination into the N-uracil amidines, providing highly functionalized pyrimido[4,5-d]pyrimidine-2,4-diones. Due to the better stability of alcohols than aldehydes, this synthetic protocol is applicable to a broad range of alcoholic substrates and does not required any protection during the whole preparation process. The presented protocol has the potential to prepare valuable products which cannot be accessed presently or extremely arduous to procure by following regular procedure. Hence, this is a remarkably improved protocol compared with the existing methodologies. The overall reaction sequence is an effective oxidation-imination-cyclization tandem process catalyzed by ruthenium catalyst.
TBHP-mediated oxidative synthesis of substituted pyrimido[4,5-: D] pyrimidines from N -uracil amidines and methylarenes under metal free conditions
Debnath, Pradip
, p. 29831 - 29839 (2019/10/01)
An efficient and operationally simple protocol has been demonstrated for the synthesis of 1,3,5,7-tetrasubstituted pyrimido[4,5-d]pyrimidines via TBHP-mediated direct oxidative coupling of N-uracil amidines and methylarenes under metal-free conditions. Du
Cyclization reactions of chloro-substituted 2-azoniaallene salts with bifunctional nucleophiles
Hamed
, p. 591 - 595 (2007/10/02)
The multifunctional electrophilic chloro-substituted 2-azoniaallene salts 3-5 react with bifunctional nucleophiles under cyclization to furnish heterocycles. Preparations of the 1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxopyrimido[4,5-d]pyrimidines 7a,b, 10a
A CONVERSION OF OXADIAZOLOPYRIMIDINE 1-OXIDES INTO PURINES
Yoneda, Fumio,Tachibana, Takako,Tanoue, Junko,Yano, Tetsumi,Sakuma, Yoshiharu
, p. 341 - 344 (2007/10/02)
Treatment of oxadiazolopyrimidine 1-oxides with amines led to the formation of the corresponding 8-substituted purine derivatives, along with other heterocyclic compounds in some cases.
