DMSO/I<sub>2</sub> mediated C–C bond cleavage of α-ketoaldehydes followed by C–O bond formation: a metal-free approach for one-pot esterification

Venkateswarlu, Vunnam; Kumar, K. Raghavendra; Gupta, Sorav; Singh, Deepika; Vishwakarma, Ram A.; Sawant, Sanghapal D.

doi:10.1039/c5ob01015b

Cited by 31 publications

(10 citation statements)

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“…(Figure 13) showed the absorption band of C=C which was observed at 1526 cm -1 and a signal was observed at 1643 cm -1 which was seen to represent the C=O bond in the ring of the suggested structure of 3-Pyridine carboxylic acid and a signal bond of C-C stretching at 879 cm -1 was observed on the IR spectrum of Compound 2 (Figure 13). IR spectrum of Compound 2 is similar with the IR spectrum as reported by Venkateswarlu et al [19]. Tables 11 and Table 12 with the published data as reported by Venkateswarlu et al [16].…”

Section: Light Brownsupporting

confidence: 86%

Extraction, Isolation and Characterization of New Compound and Anti-Bacterial Potentials of the Chemical Constituents Compound from Leptadenia Hastata Leaf Extract

Umaru

Fa²,

Ha³

2019

Preprint

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Section: Light Brownsupporting

confidence: 86%

Extraction, Isolation and Characterization of New Compound and Anti-Bacterial Potentials of the Chemical Constituents Compound from Leptadenia Hastata Leaf Extract

Umaru

Fa²,

Ha³

2019

Preprint

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“…Later on, Sawant and co‐workers described a simple and efficient method for the CC bond cleavage followed by oxidation of the C‐1(CO)‐carbon of 2‐oxoaldehydes to form carboxylic acids. In the presence of DMSO and iodine, the reaction proceeded with excellent yields (Scheme ) 66…”

Section: As Oxidantmentioning

confidence: 99%

The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis

2016

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Dimethyl sulfoxide (DMSO) is one of the most commonly applied organic solvents in chemical transformationsa nd is utilized widely in industrial processesa sw ell. During the past decades,n umerous procedures using DMSO as ar eaction reagent have been developed and published.I nt his review,t he main developmentso nt he employment of DMSOa s sources of À Me, À SMe, À SO 2 Me,a sa no xidant etc. have been summarized and discussed.1I ntroduction 2A sC 1 Sources 2.1 As À CH 3 S ource 2.2 As À CH 2 À S ource 2.3 As À CH À S ource 2.4 As À CHO Source 2.5 As À CNS ource 3A s S(O) x Me Sources 3.1 As À SMe Source 3.2 As À SO 2 Me Source 4A sO xidant 4.1 As Oxygen Source 4.2 As Oxidant 5C onclusions

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“…By comparing the spectroscopic data (mainly 1 H and 13 C NMR) with reported data, the known compounds were identified as cinnzeylanol (8), 34 cinnacaside (9), 35 kelampayoside A (10), 23 syringaresinol (11), 36 cinnzeylanin, 34 anhydrocinnzeylanol, 37 anhydrocinnzeylanine, 38 2-methoxycinnamaldehyde, 39 2-hydroxycinnamaldehyde, 40 cinnamyl alcohol, 41 cinnamic acid, 32 2-hydroxycinnamyl alcohol, 42 coniferyl aldehyde, 43 rosavin, 44 (2E)-3-phenyl-2propen-1-yl 6-O-β-Dxylopyranosyl-β-D-glucopyranoside, 44 1-phenyl-1,2,3-propanetriol, 42 guaiacylglycerol, 45 guaialcylglycerol 7-O-β-D-glucopyranoside, 46 erythro-syringylglycerol, 45 dihydrocinnacasside, 19 cryptamygin C, 29 3,4-dimethoxyphenyl 1-O-D-apio-β-D-furanosyl-β-D-glucopyranoside, 23 canthoside C, 47 cinnacassosides C, 23 coumarin, 48 benzoic acid, 49 syringaldehyde, 50 (−)-lyoniresinol 2α-O-β-D-glucopyranoside, 51 (4R)-4-hydroxy-1,10-secomuurol-5ene-1,10-dione, 52 decumbic acid, 53 Analgesic Effects of the Isolates. Among the isolates from the bark of C. cassia, cinnzeylanol (8), cinnacaside (9), kelampayoside A (10), syringaresinol (11), cinnzeylanin, cryptamygin C, 3,4-dimethoxyphenyl 1-O-D-apio-β-D-furanosyl-β-D-glucopyranoside, and syringaldehyde were evaluated for their analgesic effects in a paclitaxel-induced cold allodynia mice model.…”

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Aromatic and Aliphatic Apiuronides from the Bark of Cinnamomum cassia

Chang

Lee

et al. 2021

J. Nat. Prod.

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Cinnamomum cassia Presl (Cinnamon) has been widely cultivated in the tropical or subtropical areas, such as Yunnan, Fujian, Guandong, and Hainan in China, as well as India, Vietnam, Thailand, and Malaysia. Four new glycosides bearing apiuronic acid (1, 4, 6, and 7) and their sodium or potassium salts (2, 3, and 5), together with 31 known compounds, were isolated from a hot water extract of the bark of C. cassia via repeated chromatography. The structures of the new compounds (1−7) were determined by NMR, IR, MS, and ICP-AES data and by acid hydrolysis and sugar analysis. This is the first report of the presence of apiuronic acid glycosides. Some of the isolates were evaluated for their analgesic effects on a neuropathic pain animal model induced by paclitaxel. Cinnzeylanol (8), cinnacaside (9), kelampayoside A (10), and syringaresinol (11) showed analgesic effects against paclitaxelinduced cold allodynia.A member of the Lauraceae family, Cinnamomum cassia Presl (Cinnamon) is a medium sized evergreen tree. 1 C. cassia originated in Southern China and can be widely cultivated in the Yunnan, Fujian, Guandong, and Hainan provinces of China, as well as in Thailand, Malaysia, Laos, India, Indonesia, and Vietnam. 2 Chinese cinnamon has been commonly used for centuries as a flavoring agent for desserts, pastries, and meat in Asia, Europe, and the Americas. 3 The bark of C. cassia (cinnamon) has been used as a traditional medicine to treat amenorrhea, gastrointestinal neurosis, cardiac palpitations diarrhea, edema, dysmenorrhea, rheumatoid arthritis, impotency, and diabetes. 4−6 The aqueous extract of cinnamon has been reported to exhibit potent anticomplement, immunosuppressive, antioxidant, antiproliferative, angiogenesis, antinociceptive, and anti-inflammatory activities and induced apoptosis. 7−13 The bark of C. cassia represents one of the major sources of phenolic compounds, and there are various secondary metabolites such as diterpenoids, 14−16 phenylpropanoids, 17−19 flavonoids, 20 lignans, 20,21 sesquiterpenoids, 22 and other compounds. 23,24 In a previous study, it was found that a hot water extract of the bark of C. cassia exhibited a relieving effect on cold allodynia induced by anticancer drugs. It was found that a major compound in C. cassia, coumarin, played a role in this analgesic effect. 25 Thus, we focused on secondary metabolites in the hot water extract with ameliorating effects against cold allodynia induced by paclitaxel in mice in the present work.Four new glycosides bearing apiuronic acid moieties (1, 4, 6, and 7) and their sodium or potassium salts (2, 3, and 5), together with 31 known compounds, were isolated from the hot water extract of the bark of C. cassia via repeated chromatography. The structures of the new compounds and their sodium or potassium salt forms were elucidated using spectroscopic [ 1 H NMR, 13 C NMR, 2D NMR, MS, IR, and inductively coupled plasma atomic emission spectroscopy (ICP-AES)] data, and the structures of the known compounds were identified by comparing spectroscop...

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DMSO/I₂ mediated C–C bond cleavage of α-ketoaldehydes followed by C–O bond formation: a metal-free approach for one-pot esterification

Cited by 31 publications

References 51 publications

Extraction, Isolation and Characterization of New Compound and Anti-Bacterial Potentials of the Chemical Constituents Compound from Leptadenia Hastata Leaf Extract

Extraction, Isolation and Characterization of New Compound and Anti-Bacterial Potentials of the Chemical Constituents Compound from Leptadenia Hastata Leaf Extract

The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis

Aromatic and Aliphatic Apiuronides from the Bark of Cinnamomum cassia

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DMSO/I2 mediated C–C bond cleavage of α-ketoaldehydes followed by C–O bond formation: a metal-free approach for one-pot esterification

Cited by 31 publications

References 51 publications

Extraction, Isolation and Characterization of New Compound and Anti-Bacterial Potentials of the Chemical Constituents Compound from Leptadenia Hastata Leaf Extract

Extraction, Isolation and Characterization of New Compound and Anti-Bacterial Potentials of the Chemical Constituents Compound from Leptadenia Hastata Leaf Extract

The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis

Aromatic and Aliphatic Apiuronides from the Bark of Cinnamomum cassia

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Product

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DMSO/I₂ mediated C–C bond cleavage of α-ketoaldehydes followed by C–O bond formation: a metal-free approach for one-pot esterification