1357830-08-0Relevant articles and documents
Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
Senadi, Gopal Chandru,Kudale, Vishal Suresh,Wang, Jeh-Jeng
, p. 979 - 985 (2019/03/12)
Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.
Concise Synthesis of Dictyoquinazol A via a Dimerisation-Cyclocondensation Sequence
Wangsahardja, Jonatan,Marcolin, Gabriella M.,Lizarme, Yuvixza,Morris, Jonathan C.,Hunter, Luke
, p. 1237 - 1240 (2016/05/10)
A two-step total synthesis of the neuroprotective alkaloid, dictyoquinazol A, has been achieved. The brevity of this synthesis was enabled by exploiting the hidden symmetry of the target molecule. Several structural analogues were also prepared using a similar strategy. These results provide a platform for future structure-activity relationship studies in the quest for a novel treatment for stroke.
Synthesis of 3-substituted and 2,3-disubstituted quinazolinones via Cu-catalyzed aryl amidation
Xu, Lanting,Jiang, Yongwen,Ma, Dawei
supporting information; experimental part, p. 1150 - 1153 (2012/03/27)
CuI/4-hydroxy-l-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide takes place at 80 °C, affording 3-substituted quinazolinones directly. Under these conditions other amides that were tested only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via HMDS/ZnCl2 mediated condensative cyclization.
