A facile synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines through NHC-catalyzed cascade annulations

Yao, Changsheng; Jiao, Weihui; Xiao, Zhaoxin; Xie, Yuanwei; Li, Tuanjie; Wang, Xiang‐Shan; Liu, Rui; Yu, Chenxia

doi:10.1039/c3ra41935e

Cited by 18 publications

(17 citation statements)

References 51 publications

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“…In addition, similar reactivity and yields were obtained using 1,2-diaminoethane, 1,3-diaminpropane and 2,2-dimethyl-1,3diaminopropane. The structures of all desired products 4a-m were confirmed by FT-IR and 1 H and 13 C NMR spectroscopy and CHN analyses (supporting information). The 1 H NMR spectra showed four characteristic signals; two signals between 5.00 and 6.50 ppm for the aliphatic CH resonances of the 3,4-dihydropyridone ring and two signals above 9.0 ppm for the NH groups of the dithiocarbamate and enamine moieties.…”

mentioning

confidence: 86%

“…Available reagents and solvents were purchased from commercial sources and were used without further purification. All 1 H and 13 C NMR spectra were recorded on a Bruker 500 MHz spectrometer and chemical shifts are reported in ppm in DMSO-d6. IR spectra were recorded on a Perkin-Elmer spectrum RX1 FT-IR spectrometer.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…: 220-222 °C; yield: 0.43 g (88%). 13 C NMR (125.7 MHz, DMSO-d6): δC = 19. 7, 39.4, 40.4, 40.8, 40.9, 60.0, 107.9, 111.1, 119.6, 128.1, 129.3, 129.7, 130.0, 133.3, 137.9, 143.8, 152.5, 167.1, 198. 8, 39.4, 39.5, 40.6, 40.8, 60.3, 108.4, 128.0, 129.3, 129.3, 129.7, 130.7, 132.9, 136.8, 138.0, 152.5, 167.3, 198.8 13 C NMR (125.7 MHz, DMSO-d6): δC = 19.…”

Section: General Procedures For the Preparation Of Compounds 4a-mmentioning

confidence: 99%

“…13 C NMR (125.7 MHz, DMSO-d6): δC = 19. 7, 39.4, 40.4, 40.8, 40.9, 60.0, 107.9, 111.1, 119.6, 128.1, 129.3, 129.7, 130.0, 133.3, 137.9, 143.8, 152.5, 167.1, 198. 8, 39.4, 39.5, 40.6, 40.8, 60.3, 108.4, 128.0, 129.3, 129.3, 129.7, 130.7, 132.9, 136.8, 138.0, 152.5, 167.3, 198.8 13 C NMR (125.7 MHz, DMSO-d6): δC = 19. 3, 31.1 , 37.1, 39.0, 40.3, 59.4, 108.4, 127.6, 128.0, 128.8, 128.8, 129.3, 130.4, 133.1, 134.7, 136.6, 137.7, 152.3, 166.8, 200. 2, 40.4, 59.6, 107.4, 127.6, 128.5, 128.9, 129.3, 130.6, 130.6, 131.1, 131.6, 137.6, 138.7, 152.1, 166.7, 198.6. Anal.…”

Section: General Procedures For the Preparation Of Compounds 4a-mmentioning

confidence: 99%

“…Various methods for the synthesis of substituted bicyclic pyridones have been reported. 9 Among them, the cyclocondensation of ketenaminals with dielectrophiles such as propiolic esters, 10 diethyl but-2ynedioate, 11 β-ketoesterenol tosylates, 12 α-bromoenals, 13 azlactones, 14 itaconic anhydride 15 and other compounds 16 are extensively utilized for the synthesis of libraries of bicyclic pyridones.…”

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confidence: 99%

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Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal

Saeedi

Khoshdoun

Taheri

et al. 2021

SynOpen

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An efficient method for the synthesis of highly substituted bicyclic pyridone derivatives containing the dithiocarbamate group is reported via a one-pot three-component reaction of 2-(alkylthio)thioazlactones, diamines, and nitroketene dithioacetal in EtOH under catalyst-free conditions. The reaction proceeds via a domino amidation–intramolecular 1,4-addition-type Friedel–Crafts alkylation reaction to afford the corresponding fused bicyclic pyridones with high yields and diastereoselectivity.

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mentioning

confidence: 86%

Section: Accepted Manuscriptmentioning

confidence: 99%

Section: General Procedures For the Preparation Of Compounds 4a-mmentioning

confidence: 99%

Section: General Procedures For the Preparation Of Compounds 4a-mmentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal

Saeedi

Khoshdoun

Taheri

et al. 2021

SynOpen

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Enantioselective Synthesis of Dihydropyrazolo[3,4‐b]pyridin‐6‐ones via N‐Heterocyclic Carbene Catalyzed [3+3] Cycloaddition ofα‐Bromoenals with 5‐Aminopyrazoles

Huang

et al. 2023

Adv Synth Catal

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An N-heterocyclic carbene (NHC) catalyzed asymmetric [3 + 3] annulation of α-bromoenals with 5-aminopyrazoles is described. Using the established methodology, a structurally diverse set of high value dihydropyrazolo[3,4-b]pyridine-6ones were efficiently constructed in high yields (up to 99%) with excellent enantioselectivities (up to > 99%). The easily available starting materials, broad substrate scope, mild reaction conditions, excellent yield and enantioselectivity make this strategy attractive for the asymmetric construction of pyrazolo-fused pyridone derivatives.

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NHC‐Catalyzed Cascade Reactions for the Construction of Fused Cycles via LUMO Activation of α,β‐Unsaturated Carbonyls

Nie

2023

Asian J Org Chem

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The facile syntheses of multicyclic molecules through multi-step cascade reactions with N-Heterocyclic carbene (NHC)-catalyzed LUMO activation strategies are summarized. The reaction mechanisms involved in these cascade catalytic transformations are also provided and discussed. The review article is arranged according to the reaction starting materials that are used for the NHC-catalytic activation processes.

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A facile synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines through NHC-catalyzed cascade annulations

Cited by 18 publications

References 51 publications

Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal

Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal

Enantioselective Synthesis of Dihydropyrazolo[3,4‐b]pyridin‐6‐ones via N‐Heterocyclic Carbene Catalyzed [3+3] Cycloaddition ofα‐Bromoenals with 5‐Aminopyrazoles

NHC‐Catalyzed Cascade Reactions for the Construction of Fused Cycles via LUMO Activation of α,β‐Unsaturated Carbonyls

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