A short and efficient synthetic protocol for the synthesis of 5-substituted-4,6-dioxo-pyrrolo[2,3-d]pyrimidines

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

“…The pyrrolopyrimidine is an important class of N ‐heterocyclic compounds which has displayed various biological activities such as antibacterial, anti‐HIV type, anti‐microbial, anti‐fungal, anti‐viral, antitumor, and antiinflammatory, properties. In addition, pyrrolo[1,2‐ a ]pyrimidine framework is an important structural part of some pigments and dyes for plastics .…”

“…In 2011, Sekhar et al. have reported cyclocondensation of α , α ‐dibromoaldehydes with 2,4‐diamino‐6‐hydroxypyrimidine at basic media, in 2012 pyrrolo[1,2‐ a ]pyrimidin‐10‐one dyes were obtained from the reaction between oxalyl chloride and heterocyclic ketene aminals (HKAs) containing pyrimidine ring at 50 °C . In 2012 Rad‐Moghadam and Azimi were reported synthesis of oxindolylpyrrolo[2,3‐ d ]pyrimidines via a three‐component sequential tandem reaction of acetophenone, isatin and 6‐aminouracil by use of catalytic amount of piperidine and p ‐toluenesulfonic acid, in 2013 these type of products were synthesized with domino coupling of 6‐aminouracil, aldehydes, and nitromethane in the presence of CuFe 2 O 4 magnetic nanoparticles as catalyst .…”

Synthesis and Biological Evaluation of Bromo‐ and Fluorodanicalipin A

“…Tr eatment of 5 with Br 2 led to the geminal dibromide. [8] Ther esulting unpurified product was directly reduced and protected to give 6.Athree step sequence consisting of pivalate cleavage,o xidation of the liberated alcohol and aldoxime formation afforded fragment 7.…”

Synthesis and Biological Evaluation of Bromo‐ and Fluorodanicalipin A

“…[8] Ther esulting unpurified product was directly reduced and protected to give 6.Athree step sequence consisting of pivalate cleavage,o xidation of the liberated alcohol and aldoxime formation afforded fragment 7. After protection of the primary alcohol, the alkene was converted into 5 via hydroboration and subsequent Swern oxidation.…”

“…= 76:24, 95 % ee;e )TBSOTf (1.3 equiv), Et 3 N(1.5 equiv), CH 2 Cl 2 ,08 8C; f) Mo(CO)8 (1.2 equiv), MeCN/H 2 O(10:1), 90 8 8C; g) iPrCHO (11 equiv), SmI 2 (0.09 m in THF, 30 mol %), THF, À30 8 8C; h) (iBu) 2 AlH (3.0 equiv), CH 2 Cl 2 , À78 8 8C, 67 %o ver 4steps;i )CBr 4 (4.9 equiv), PPh 3 (5.4 equiv), pyridine (13 equiv), CH 2 Cl 2 ,RT, 45 %; j) HF·pyridine (33 equiv),T HF, 0 8 8Ct oRT, 99 %; k) PhNMe 3 Br 3 (1.4 equiv), CH 2 Cl 2 ,08 8Ct oRT, 99 %, d.r. = 76:24, 95 % ee;e )TBSOTf (1.3 equiv), Et 3 N(1.5 equiv), CH 2 Cl 2 ,08 8C; f) Mo(CO)8 (1.2 equiv), MeCN/H 2 O(10:1), 90 8 8C; g) iPrCHO (11 equiv), SmI 2 (0.09 m in THF, 30 mol %), THF, À30 8 8C; h) (iBu) 2 AlH (3.0 equiv), CH 2 Cl 2 , À78 8 8C, 67 %o ver 4steps;i )CBr 4 (4.9 equiv), PPh 3 (5.4 equiv), pyridine (13 equiv), CH 2 Cl 2 ,RT, 45 %; j) HF·pyridine (33 equiv),T HF, 0 8 8Ct oRT, 99 %; k) PhNMe 3 Br 3 (1.4 equiv), CH 2 Cl 2 ,08 8Ct oRT, 99 %, d.r.…”