Synthetic Communications

doi: 10.1080/00397910600978598pmid: N/A

Graphical Abstract Section

Yang, Xiaoming; Zou, Xiaomin; Fu, Yiqiu; Mou, Ke; Fu, Gang; Ma, Chao; Xu, Ping

doi: 10.1080/00397910600977509pmid: N/A

Abstract β‐Secretase inhibitors with a Leu*Ala hydroxyethylene dipeptide (HED) isostere have been an especially interesting topic in recent years. In this study, a template compound 17 was synthesized, featuring truncation at the P2′ position and changes at P2 and P3, which differs from other reported potent inhibitors. The purpose was to explore optimal reaction conditions and construct an inhibitor library to investigate ideal protein–substrate interaction.

Zhang, Hui; Cao, Weiguo; Ma, Dawei

doi: 10.1080/00397910600977533pmid: N/A

Abstract An improved, mild procedure for the CuI‐catalyzed coupling reactions of aryl iodides with aliphatic and aromatic thiols, using L ‐proline as the ligand, is reported. This procedure is noteworthy given its high generality and exceptional level of functional group toleration.

Yu, Jindi; Lian, Gaoyan; Zhang, Danwei

doi: 10.1080/00397910600977574pmid: N/A

Abstract Methyl 3‐(tert‐butyl((E)‐3‐(2,2‐diphenylcyclopropyl)‐2‐propenyl)amino)‐3‐oxo‐2‐(phenylseleno)propanoate was prepared in 10 steps in good to excellent yield using benzophenone and hydrazine hydrate as the starting materials.

Chen, Wei‐Yi; Qin, Su‐Dong; Jin, Jian‐Rong

doi: 10.1080/00397910600977632pmid: N/A

Abstract Sulfamic acid efficiently catalyzes the three‐component condensation reaction of aldehydes, 1,3‐dicarbonyl compounds, and urea/thiourea under solvent‐free conditions to afford the corresponding dihydropyrimidinones and thio‐derivatives in high yields. Silica sulfuric acid is also found to be an efficient catalyst for the Biginelli reaction under solvent‐free conditions. Compared to the classical Biginelli reaction conditions, this new method consistently has the advantage of giving good yields and requiring short reaction times.

Chen, Wei‐Min; Wan, Shan‐He

doi: 10.1080/00397910600978085pmid: N/A

Abstract The synthesis of 2‐amino‐6‐methyl‐5‐(pyridin‐4‐ylsulfanyl)‐3H‐quinazolin‐4‐one (1) was studied via three different synthetic routes starting from 4‐bromo‐5‐methylisatin. The best route was established, which is a straightforward route via 2‐guanidino‐5‐bromo‐6‐methyl‐quinazolin‐4‐one (6) as the key intermediate and a one‐pot synthesis by treatment of compound 6 with 4‐mercaptopyridine and KOH via the Ullmann reaction. When removing the amidino group from 2‐guanyl of compound 6 under strong alkaline conditions, surprisingly we found that 4‐mercaptopyridine could prevent the bromo group on a quinazoline ring from substitution by a hydroxyl group. Furthermore we found that 4‐mercaptopyridine analogues such as hydroxypyridinones also play a role of protecting agent in such a reaction system.

Zhang, Bang‐Le; Wang, Fang‐Dao; Yue, Jian‐Min

doi: 10.1080/00397910600978093pmid: N/A

Abstract A method for the rapid synthesis of psoralen and 4‐methylpsoralen has been developed. The key intermediates, coumarinyloxyaldehydes, were obtained in only two steps from the easily available starting materials, 7‐hydroxycoumarin derivatives, by an oxidative procedure. By using Swern oxidation, psoralen and 4‐methylpsoralen were finally produced in the overall yields of 71% and 67%, respectively.

Deng, Shi‐Ren; Wu, Tao; Hu, Gao‐Qiang; Li, Dan; Zhou, Yun‐Hong; Li, Zao‐Ying

doi: 10.1080/00397910600978101pmid: N/A

Abstract A novel trisulfide‐containing thiophene, 1,5‐dihydrothieno[3,4‐e][1,2,3]trithiepine (5), and a disulfide analogue, 1,4‐dihydrothieno[3,4‐d][1,2]dithiine (4), were designed and synthesized. All the compounds were characterized by FT‐IR, NMR, Raman, MS, and elemental analysis, some of which were confirmed by single‐crystal structure analysis. The designed molecules have potential usage as the cathode material for batteries.

Yang, Fafu; Ji, Yanqing; Guo, Hongyu; Lin, Jianrong; Peng, Qi

doi: 10.1080/00397910600978150pmid: N/A

Abstract A series of novel calix[4](aza)crowns 2a–2d containing acylhydrazone groups was designed and synthesized via 1+1 condensation of calix[4]‐1,3‐substituted benzaldehyde derivative 1 with bis‐hydrazides in 85–90% yields. They showed good complexation abilities toward α‐amino acids and exhibited complexation selectivity toward tryptophane.

Chan Lee, Jong; Jung Park, Hyun

doi: 10.1080/00397910600978168pmid: N/A

Abstract A facile and efficient method for the α‐halogenation of carbonyl compounds utilizing N‐halosuccinimides (NXS) in the presence of urea–hydrogen peroxide (UHP) in [bmim]BF4 has been newly developed.