Generation of pyrrolo[2,3-d]pyrimidines. Unexpected products in the multicomponent reaction of 6-aminopyrimidines, dimedone, and arylglyoxal

Synthesis of Novel Pyrimido[4,5-b]quinolin-4-ones with Potential Antitumor Activity

“…Pyrimidinic monoamines are versatile precursors for the synthesis of heterocyclic compounds of higher complexity . For example, 6‐amino‐2‐(methylthio)pyrimidin‐4(3 H )‐one 2 and 6‐amino‐3‐methyl‐2‐(methylthio)pyrimidin‐4(3 H )‐one 3 have been used as a essential unit for the synthesis of new pyrrolopyrimidines , pyridopyrimidines and pyrimidoquinolines . On the basis of the aforementioned reports, we performed the synthesis of new pyrimidoquinolines 4a , 4b , 4c , 4d , 5a , 5b , 5c , 5d and their oxidized forms 6a , 6b , 6c , 6d , 7a , 7b , 7c , 7d according to the procedure described in Scheme .…”

5-Aminouracil as a Building Block in Heterocyclic Synthesis: Part IV. One-pot Synthesis of 1H-Pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione Derivatives Using Controlled Microwave Heating

“…With these spectroscopic data the proposed structure of 10 is identified. The formation of 10 was rationalized in terms of the initial formation of the intermediate 8 [29]. A subsequent reaction at the nucleophilic carbon atom C-6 in 5-aminouracil (1) leads to the formation of intermediate 9, which was cyclized via loss of water to finally form pyrrolopyrimidine 10 (Scheme 2).…”

A Highly Efficient Synthesis of Pyrrolo[1,2‐a]pyrimidine Derivatives Containing 1,3‐Indandione Skeleton

“…In the recent decade, several new methods have been developed and introduced for the preparation of the pyrrolo[1,2‐ a ]pyrimidine skeleton as follows: in 2010, Alizadeh et al. have reported synthesis of pyrrolo[1,2‐ a ]pyrimidines and pyrrolo[1,2‐ a ][1,3]diazepines in excellent yields, using diverse diamines, 1,1‐bis(methylthio)‐2‐nitroethen and diaroylacetylene in EtOH at reflux, in 2010 these type of products were synthesized with three‐component reaction of aminopyrimidines, dimedone, and arylglyoxales in the presence of acetic acid as catalyst at reflux . In 2011, Sekhar et al.…”