107407-80-7Relevant articles and documents
Improved synthesis of pyrrolo[1,2-c]pyrimidine and derivatives
Minguez, Jose M.,Vaquero, Juan J.,Garcia-Navio, Jose L.,Alvarez-Builla, Julio
, p. 4263 - 4266 (1996)
An improved synthesis of pyrrolo[1,2-c]pyrimidine derivatives by cyclocondensation of pyrrole-2-carboxaldehydes with tosylmethyl isocyanide followed by desulfonylation of the resulting 2-tosylpyrrolo[1,2-c]- pyrimidines with sodium amalgam is described.
Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines
Baumann, Marcus,Rodriguez Garcia, Antonio M.,Baxendale, Ian R.
supporting information, p. 4231 - 4239 (2015/04/14)
The efficient flow synthesis of important heterocyclic building blocks based on the 1,2,4-triazole and pyrrolo[1,2-c]pyrimidine scaffold has been achieved. Crucially, a telescoped continuous flow process was developed based on the reaction of N-formylglycine with triphosgene to deliver a stream of ethyl isocyanoacetate in situ, which subsequently yielded the desired heterocyclic entities in a telescoped reaction. Additionally, the functionalisation of the pyrrolo[1,2-c]pyrimidine core via subsequent SEAr reactions was studied revealing insight into a 'halogen dance' phenomenon associated with these medicinally relevant architectures. This journal is
Pyrrolodiazines. 5. Synthesis, structure, and chemistry of pyrrolo[1,2- c]pyrimidine. Dipolar cycloaddition of pyrrolo[1,2-c]pyrimidinium ylides
Minguez, Jose M.,Vaquero, Juan J.,Alvarez-Builla, Julio,Castano, Obis,Andres, Jose L.
, p. 7788 - 7801 (2007/10/03)
An improved synthesis of pyrrolo[1,2-c]pyrimidines, including the parent system, was accomplished via sequential condensation of substituted pyrrole- 2-carboxaldehydes with tosylmethyl isocyanide (TOSMIC), followed by desulfonylation of the formed tosylpyrrolo[1,2-c]pyrimidines. Based on the ab initio calculations performed on the pyrrolo[1,2-c]pyrimidine 1a, some of the basic chemistry was investigated, including electrophilic substitution, addition of organolithium reagents, metalation with lithium diisopropylamide (LDA) and subsequent reaction with electrophiles, and formation of salts by quaternization of the nonbridgehead nitrogen. Azomethine ylides generated from pyrrolo[1,2-c]pyrimidinium salts undergo 1,3-dipolar cycloaddition with suitable dipolarophiles to give new dipyrrolo[1,2-a;1',2'-c]pyrimidine derivatives, with high regio- and stereoselectivity.
