Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)

Bahrami, Kiumars; Khodaei, Mohammad Mehdi; Targhan, Homa; Arabi, Mehdi Sheikh

doi:10.1016/j.tetlet.2013.07.033

Cited by 27 publications

(8 citation statements)

References 46 publications

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“…Method A; Yield 95%; Mp. 196 °C (183 °C [56], 190–193 °C [60], 187–189 °C [61]; R f = 0.69; IR (Zn/Se ATR, cm − 1 ): 3227 m , 3180 w , 3111 w , 3031 w , 2909 w , 1651 s , 1598 s , 1532 s , 1514 s , 1404 m , 1322 s , 1301 m , 1257 m , 817 m , 805 s , 778 s , 747 s , 730 m ; 1 H-NMR (DMSO- d 6 ) [58,59], δ: 10.51 (s, 1H), 8.21–8.16 (m, 1H), 8.07 (d, J = 8.4 Hz, 1H), 8.05–8.00 (m, 1H), 7.74 (dd, J = 7.0 Hz, J = 1.1 Hz, 1H), 7.71 (d, J = 8.1 Hz, 2H), 7.64–7.55 (m, 3H), 7.18 (d, J = 8.4 Hz, 2H), 2.30 (s, 3H); 13 C-NMR (DMSO- d 6 ), δ: 166.97, 136.70, 134.83, 133.06, 132.53, 129.83, 129.61, 128.93, 128.16, 126.78, 126.17, 125.20, 125.03, 124.88, 119.81, 20.35; HR-MS: for C 18 H 16 NO [M+H] + calculated 262.1226 m/z , found 262.1232 m/z .…”

Section: Methodsmentioning

confidence: 99%

Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides

et al. 2014

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Abstract:In this study, a series of twenty-two ring-substituted naphthalene-1-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized carboxanilides was performed against Mycobacterium avium subsp.and N-(3-fluorophenyl)naphthalene-1-carboxamide showed against M. avium subsp. paratuberculosis two-fold higher activity than rifampicin and three-fold higher activity than ciprofloxacin. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The testing of biological activity of the compounds was completed with the study of photosynthetic electron transport (PET) inhibition in isolated spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity expressed -[4-(trifluoromethyl)phenyl]naphthalene-1-carboxamide was 59 μmol/L. The structure-activity relationships are discussed.

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Section: Methodsmentioning

confidence: 99%

Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides

et al. 2014

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“…Keberadaan gugus amidin karena sifat basa yang kuat, diharapkan dapat benar benar terprotonasi dalam kondisi biologis dan mungkin berpengaruh dalam memainkan kunci baik dalam ikatan DNA dan sel atau jaringan bioavibilitas. Penggantian gugus amidin dengan amidin dasar atau yg bukan akan menyebabkan peningkatan sitotoksisitas dalam beberapa kasus, seperti halnya senyawa turunan asam sinamat mustard bisa 20 kali lipat dari senyawa asalnya (Allen et al, 2011;Bahrami et al, 2013;Lanigan et al, 2013). Di sini, kami fokus untuk mensintesis senyawa Noktil sinnamamid dan evaluasi aktivitas sitotoksisitasnya terhadap penghambatan sel leukemia P388.…”

Section: Pendahuluanunclassified

Sintesis N-Oktilsinamamid dan Aktivitasnya terhadap Sitotoksik Sel Kanker Leukemia P388

Ernawati

Nurhalimah

Minarti

2017

JKV

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Sintesis senyawa N-Oktilsinnamamid yang diturunkan dari senyawa metil trans-sinamat dengan menggunakan katalis basa telah dilakukan. Senyawa metil sinamat terlebih dahulu dikonversi menjadi asam sinamat melalui reaksi hidrolisis dengan basa menghasilkan asam sinamat. Selanjutnya asam sinamat diamidasi dengan menggunakan oktilamin dan 1,3 disikloheksilkarboodiimide (DCC) dan 4-dimetilaminopiridin (DMAP) sebagai katalis. Dari penelitian ini diperoleh rendemen hasil sintesis asam sinamat, sintesis N-Oktilsinnamami yang cukup baik. Hasil reaksi diidentifikasi dengan menggunakan 1H-NMR, 13C-NMR dan LC-MS. Uji sitotoksik senyawa N-Oktilsinamamid terhadap sel leukemia P388 diperoleh nilai IC50=6.71 µg/mL. Synthesis of N-Octylcinnamamide compound derived from methyl trans-cinnamate using abase catalyst has been done. First, The compound of methyl trans-cinnamate was converted into cinnamic acid by hydrolysis reaction with an alkaline condition. Furthermore cinnamic acid was amidated by using octylamine and 1,3 dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) as a catalyst. The results of this study were obtained synthesis of cinnamic and synthesis of N-Octylcinnamamide are good enough. Identification of this product was using by 1H-NMR, 13C-NMR and LC-MS. Cytotoxic test of N-Octylcinnamamide against P388 leukemia cell was obtained IC50=6.71µg/mL.

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“…Esters are important compounds that are widely present in fine chemicals, essential oils, perfumes, cosmetics, food flavors, polymers, and many other natural products. [1][2][3] In addition, esters are also used as ap recursor in variouso rganic transformations. Generally,e sters are directly synthesized by dehydrative condensation of carboxylic acid and alcohols or from activated carboxylic acids such as acid halides, anhydrides, esters, and amides under acidic or basic conditions.…”

Section: Introductionmentioning

confidence: 99%

Solvent‐free, l‐Leucine‐Catalyzed Direct Dehydrative Esterification of Carboxylic Acids with Alcohols: Direct Synthesis of 3‐Alkoxy 1(3 H)‐isobenzofuranone

et al. 2017

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Al -leucine-catalyzed mild and efficient method has been developed for the synthesis of open-chain as well as cyclic esters. Aw ider ange of alcohols, including primary, secondary,a nd tertiaryw ith aliphatic and aromatic side chains, were successfully tolerated. In the case of 2-carboxybenzaldehydes with different alcohols, 3-alkoxy-1-(3 H)-isobenzofuranones were obtained in good yields. Alcohols from natural origin have also been reacted with various acids successfully to get the corresponding esters. The reaction proceeded under neat conditions and there is no need for any acid, base, or removal of water during the reaction.

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Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)

Cited by 27 publications

References 46 publications

Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides

Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides

Sintesis N-Oktilsinamamid dan Aktivitasnya terhadap Sitotoksik Sel Kanker Leukemia P388

Solvent‐free, l‐Leucine‐Catalyzed Direct Dehydrative Esterification of Carboxylic Acids with Alcohols: Direct Synthesis of 3‐Alkoxy 1(3 H)‐isobenzofuranone

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