N-Iodosuccinimide involved one-pot metal-free synthesis of 2-heteroaromatic benzothiazole compounds

Chu, Xianglong; Duan, Tiantian; Luo, Xuan; Feng, Lei; Jia, Jiong; Ma, Chen

doi:10.1039/c6ob02731h

Cited by 14 publications

(2 citation statements)

References 32 publications

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“…Therefore, the development of more general methods for improving the structural diversity is highly desirable. In continuation of our previous efforts on direct C–H bond functionalization, we herein report an environment-friendly and efficient functionalization of C(sp 3 )–H bonds and tandem cyclization strategy from 2-methylbenzothiazoles or 2-methylquinolines and 2-styrylanilines by iodide catalysis to formation of functionalized quinoline derivatives (Scheme b). This protocol features metal-free, direct functionalization of C(sp 3 )–H bonds, broad substrate scope, moderate-to-good yields, and scaled-up synthetic capability.…”

Section: Introductionmentioning

confidence: 93%

Metal-Free Synthesis of Functionalized Quinolines from 2-Styrylanilines and 2-Methylbenzothiazoles/2-Methylquinolines

Chu

2023

ACS Omega

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A facile functionalization of C(sp3)–H bonds and tandem cyclization strategy to synthesize quinoline derivatives from 2-methylbenzothiazoles or 2-methylquinolines and 2-styrylanilines has been developed. This work avoids the requirement for transition metals, offering a mild approach to activation of C(sp3)–H bonds and formation of new C–C and C–N bonds. This strategy features excellent functional group tolerance and scaled-up synthetic capability, thus providing an efficient and environmentally friendly access to medicinally valuable quinolines.

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Section: Introductionmentioning

confidence: 93%

Metal-Free Synthesis of Functionalized Quinolines from 2-Styrylanilines and 2-Methylbenzothiazoles/2-Methylquinolines

Chu

2023

ACS Omega

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“…As far as the catalytic system is concerned, various catalysts such as elemental sulfur, [55,60] NH 4 SCN, [61] NH 4 I, [62] Fe(SD) 3 , [63] NaSH, [64] VOSO 4 , [65] Brönsted acid surfactant combined ionic liquid, [66] Al(HSO 4 ) 3 , [67] Riboflavin, [68] Lanthanum (III) nitrate hexahydrate, [69] I 2 , [70] N-Iodosuccinimide (NIS), [71] Iron/S 8 , [72] Cu, [73] Pd, [74] TEMPO ((2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl radical), [75] Baker's yeast, [76] NaHSO 4 , [77] Ag 2 O, [78] etc. have been recently explored in the synthesis of benzothiazole and its derivatives.…”

Section: Conventional Protocols For the Synthesis Of 2-substituted Benzothiazolesmentioning

confidence: 99%

Solid‐Supported Materials‐Based Synthesis of 2‐Substituted Benzothiazoles: Recent Developments and Sanguine Future

et al. 2021

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Benzothiazole and its derivatives have been manifested as an optimistic scaffold due to their immense biological importance. Several methodologies have been reported as modifications after the first report of 2-substituted benzothiazole. Among them, many involve a shift from the conventional synthetic approach by utilizing different catalytic systems. Moreover, synthetic methodologies focused on improvements in terms of product yield, reaction duration, use of environmentally benign conditions and simplified workup procedures predominate among the recently developed approaches. Solid-phase organic synthesis received considerable attention with the pioneering findings of Merrifield's solid-phase peptide synthesis in 1963. A diverse range of organic, inorganic and organic-inorganic substances have been utilized as polymeric solid supports in various catalytic applications. The recyclability and reusability of the immobilized catalysts over consecutive cycles establish them as an attractive alternative over conventional catalytic systems from the environment as well as industrial perspective. The present review summarizes the recent developments in the environmentally benign synthesis of benzothiazole derivatives using supported reagents. Different solid supports along with their catalytic application, mechanistic perspective and substrate tolerance have been discussed comprehensively.

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Iodine‐Promoted Synthesis of Dipyrazolo/Diuracil‐Fused Pyridines and o‐Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4‐Methylazaarenes

et al. 2021

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The iodine‐promoted oxidative domino annulation and carbonylation process has been developed for the synthesis of biologically important azaarene‐substituted bis‐pyrazolo[3,4‐b:4′,3′‐e]pyridines (BPPs), diuracilpyridines and o‐amino diheteroaryl ketones. The domino procedure proceeded with easily available methyl azaarenes, 5‐aminouracils and substituted 5‐aminopyrazoles. This protocol is a simple and metal‐free approach which exhibits high functional group compatibility and broad substrates scope. Moreover, this transformation can be applied for the preparation of dipyrazolo/diuracil‐fused pyridines on a gram scale.

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N-Iodosuccinimide involved one-pot metal-free synthesis of 2-heteroaromatic benzothiazole compounds

Cited by 14 publications

References 32 publications

Metal-Free Synthesis of Functionalized Quinolines from 2-Styrylanilines and 2-Methylbenzothiazoles/2-Methylquinolines

Metal-Free Synthesis of Functionalized Quinolines from 2-Styrylanilines and 2-Methylbenzothiazoles/2-Methylquinolines

Solid‐Supported Materials‐Based Synthesis of 2‐Substituted Benzothiazoles: Recent Developments and Sanguine Future

Iodine‐Promoted Synthesis of Dipyrazolo/Diuracil‐Fused Pyridines and o‐Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4‐Methylazaarenes

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