The reaction of β‐naphthol with nitrostyrene derived primary MBH acetates in presence of Cs2CO3 as base resulted in the formation of 3‐nitro‐4‐phenyl‐3,4‐dihydro‐2H‐naphthopyran as the major isomer via SN2′ process. Due to the bis‐electrophilic nature of MBH acetates, the minor product 3‐nitro‐2‐phenyl‐3,4‐dihydro‐2H‐naphthopyran was also obtained presumably due to SN2 process with γ
‐attack on MBH acetates. The state of the art density functional theory (DFT) calculations were carried out to account for these competitive pathways towards the formation of major and minor products.
A convenient, efficient method for synthesising indole-3-substituted-2-benzimidazoles and benzothiazoles was carried out using N-arylation followed by condensation-oxidation protocol. N-arylation of 1H-indole-3-carbaldehyde was carried out via CuI/DMED to yield 1-(3-((tert-butylsulfonyl)methyl)phenyl)-1H-indole-3-carbaldehyde. Condensation using various o-phenylenediamines in the presence of CAN/DMF as oxidant furnished the desired 2-(1-(3-((tert-butylsulfonyl)methyl)phenyl)-1H-indol-3-yl)-1H-benzo[d]imidazole. In addition to simple o-phenylenediamines, 1,2-arylenediamines substituted with withdrawing and donating groups, heterocyclic-2,3-phenylene diamines are well tolerated and give good yields of up to 74% yield. As simple reaction between o-phenylenediamines and 1H-substituted indole-3-carboxyaldehyde give indole-3-substituted-2-benzimidazoles with moderate to good yields. These novel indole-derived benzimidazoles and benzothiazoles have shown their efficacy as anti-cancer agents with various cancer K-562, MDA-MB231, colon-205 cell lines.
Synthesis of N-(1R,2S)-2-(bromo-3-oxo-1,3-diphenylpropyl)-4-methylbenzene sulfonamide and N-(1R,2S)-(2-bromo-3-oxo-1,3-diphenylpropyl)-4-methylbenzene sulfonamide was carried out by a three component reaction using phenacyl bromide, p-toluenesulfonamide and carboxyaldehyde in presence of mild Lewis acid such as BF3·(OEt)2 in dichloromethane. The synthetic utility of this protocol was carried out with syn-isomer to yield corresponding cis-aziridines. This protocol was operationally simple for a wide variety of substituted carboxaldehydes and substituted phenacyl bromides.
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