Nef‐Isocyanide ‐Based One‐pot Two‐step Three Component Dihydrobenzo[4,5]Imidazo[2,1‐b]thiazoles Synthesis

Abstract

The reactive imidoyl chloride adducts generated in situ from the reaction of isocyanide and acyl chlorides were trapped by 2‐mercaptobenzimidazoles to yield highly functionalized dihydrobenzo[4,5]imidazo[2,1‐b]thiazoles in good yields.

Identifying a Hidden Conglomerate Chiral Pool in the CSD

“…Within this list are C 2 symmetrical pyrimidine (OBIPAR 122 ), phosphine (LUSZOO 123 ), and imidazole (ROJPOW 124 ) ligands, an atropisomeric quinoline (TUWFAT 125 ), an α-methylpyridine (DOBWUN 126 ), and a chiral salen ligand (TUNMOF 127 ). Potential types of organocatalysts such as the C 2 symmetrical diol (NULZEA 128 ), a PTC (phase transfer catalyst) crown ether (NOCNIC 129 ), a chiral phosphoric acid (CUVGAB 130 ), chiral ureas (RIPBUN, 131 AZUDAB 132 ), benzotetramisole (YAMBAS 133 ), amino-alcohol (HARFEN 134 ), and imidazole (PURJUJ 135 ) may also find use in asymmetric synthesis. These are only selected examples, and we would encourage the community to view our full list of structures to ascertain which compounds they may deem useful to their research.…”

“… Potential ligands and organocatalysts from conglomerate crystals. The following crystal structures, labeled by their CSD Refcode, were identified as conglomerates: OBIPAR, 122 LUZOO, 123 PURJUJ, 135 NULZEA, 128 KAQMEV, 167 DOBWUN, 126 ROJPOW, 124 TUWFAT, 125 HARFEN, 134 YAMBAS, 133 CUVGAB, 130 GADTIR, 168 NOCNIC, 129 TUNMOF, 127 QEVSAO, 169 VARLIK, 170 RIPBUN, 131 AZUDAB. 132 …”

“…Potential ligands and organocatalysts from conglomerate crystals. The following crystal structures, labeled by their CSD Refcode, were identified as conglomerates: OBIPAR, 123 LUZOO, 124 PURJUJ, 136 NULZEA, 129 KAQMEV, 168 DOBWUN, 127 ROJPOW, 125 TUWFAT, 126 HARFEN, 135 YAMBAS, 134 CUVGAB, 131 GADTIR, 169 NOCNIC, 130 By tracking materials which undergo this type of crystallization, the possibility of exploiting a powerful mode of chiral amplification can be achieved, whereby a substrate is able to bias its own enantioenrichment. The exciting synthetic potential of conglomerate crystallization has been demonstrated in the case of the natural product Narwedine.…”

A Potentially Limitless Chiral Pool via Conglomerate Crystallisation: Unidentified Spontaneous Resolution in the CSD.

“…Within this list are C2 symmetrical pyrimidine (OBIPAR [76] ), phosphine (LUSZOO [77] ) and imidazole (ROJPOW [78] ) ligands, an atropsiomeric quinoline (TUWFAT [79] ), an α-methylpyridine (DOBWUN [80] ), and a chiral salen ligand (TUNMOF [81] ). Potential types of organocatalysts such as the C2 symmetrical diol (NULZEA [82] ), a PTC (phase transfer catalyst) crown ether (NOCNIC [83] ), and chiral phosphoric acid (CUVGAB [84] ), chiral ureas (RIPBUN, [85] AZUDAB [86] ), benzotetramisole (YAMBAS [87] ), amino-alcohol (HARFEN [88] ), and imidazole (PURJUJ [89] ) may also find use in asymmetric synthesis. These are only selected examples, and we would encourage the community to view our full list of structures they may deem useful to their research.…”