A Convenient Method for the Synthesis of Carboxylic Esters

Mukaiyama, Teruaki; Usui, Masahiro; Shimada, E.; Saigo, Kazuhiko

doi:10.1246/cl.1975.1045

Cited by 217 publications

(109 citation statements)

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“…4-Cl-IAA (2) was coupled with methyl Llactate (5a), providing methyl O-(4-chloroindole-3-acetyl)-Llactate (1b) in good yield, by dehydration with Mukaiyama's reagent (2-chloro-1-methylpyridinium iodide) in the presence of triethylamine. 17) Methyl and ethyl L-lactate esters of 4-Cl-IAA were also prepared by coupling with N,NЈ-dicyclohexylcarbodiimide (DCC) as the condensing agent. The pyridinium salt is more advantageous for purification of the lactate ester after coupling than is DCC as the condensing agent.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and plant growth-regulating activities of L-lactic acid derivatives of 4-chloroindole-3-acetic acid

et al. 2006

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Introduction4-Chloroindole-3-acetic acid (4-Cl-IAA), isolated from immature seeds of Pisum sativum, [1][2][3] has strong hormonal activity as compared to IAA. [4][5][6][7][8][9][10][11] Its synthesis and biological activities and those of its esters also have been reported. 12,13) Root formation-promoting activities of 4-Cl-IAA and its esters are much higher than the activity of 4-(3-indole)butyric acid (IBA), the active ingredient of a commercially available root formation-promoting agent, the respective promoting activities of 4-Cl-IAA and its ethyl ester being 3.3 and 3.5 times that of IBA for Serissa japonica. 12) We are interested in massproducing tree saplings for reforestation by means of compounds that have strong root formation-promoting activity. We reported that 4-Cl-IAA, 5,6-dichoroindole-3-acetic acid (5,6-Cl 2 -IAA) and their ester derivatives are promising candidates for root formation promoters.14-16) They strongly promote the root formation of tree cuttings by both the soaking and spraying methods. In particular, root formation by spraying has an important advantage because it is easy to massproduce tree saplings for reforestation by that method.16) In root formation by Serissa plants, 4-Cl-IAA esters that bear one to three carbons in the alcohol part of the molecule also have strong root formation-promoting and other plant growthregulating activities.12,13) Our interest is in more polar derivatives bearing three carbons among esters with one to three carbons in the alcohol part of the 4-Cl-IAA ester. We selected lactic acid derivatives of 4-Cl-IAA, polar three-carbon derivatives that bond directly to 4-Cl-IAA, as new candidates for plant growth regulators. The synthesis and plant growth-regulating activities of these L-lactic acid derivatives (1a-1k) of 4-Cl-IAA are reported. The ester derivatives of 4-chloroindole-3-acetic acid (4-Cl-IAA) with L-lactic acid and L-lactic acid esters were synthesized by two schemes from 4-Cl-IAA and L-lactic acid or its esters. Their biological activities were determined by three bioassays (hypocotyl growth inhibition in Chinese cabbage (Brassica pekinensis cv. Kinshu), hypocotyl swelling and lateral root formation in black gram (Vigna mungo (L.) Hepper), and adventitious root formation in black gram cuttings). All the L-lactic acid ester derivatives had strong activities in the three bioassays, but their activities were somewhat weaker than those of 4-Cl-IAA in the first two bioassays. Root formation activity of some esters in cuttings was higher than, or the same as, that of 4-Cl-IAA. At 1ϫ10 Ϫ5 M, roots induced by the esters were about 2 to 4 times those of 4-(3-indole)butyric acid (IBA). Unexpectedly, the free lactic acid derivative had the weakest activity of all the lactic acid derivatives tested in all bioassays. Synthesis and plant growth-regulating activities of L-lactic acid derivatives of 4-chloroindole-3-acetic acid

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Section: Resultsmentioning

confidence: 99%

Synthesis and plant growth-regulating activities of L-lactic acid derivatives of 4-chloroindole-3-acetic acid

et al. 2006

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“…An anti-selective oxy-allylation reaction led to the aliphatic fragment 156a, upon treatment of PMP-protected allyl alcohol with hexanal, a strong base and the (S,S)-158 complex. Esterification of acid 155 with alcohol 156a was performed using the Mukaiyama method 106 to furnish the dienoic ester 157. RCM of 157 with second generation Grubbs catalyst afforded the eleven-membered unsaturated lactones as a 5:1 mixture of E and Z isomers, respectively.…”

Section: Aspercyclidesmentioning

confidence: 99%

Natural occurrence, biological activities and synthesis of eight-, nine-, and eleven-membered ring lactones

Ferraz¹,

Bombonato²,

Sano³

et al. 2008

Quím. Nova

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Recebido em 17/1/08; aceito em 7/4/08; publicado na web em 30/4/08 NATURAL OCCURRENCE, BIOLOGICAL ACTIVITIES AND SYNTHESIS OF EIGHT-, NINE-, AND ELEVEN-MEMBERED RING LACTONES. The natural occurrence, biological activities and synthetic approaches to natural eight-, nine-, and elevenmembered lactones is reviewed. These medium ring lactones are grouped according to ring size, and their syntheses are discussed. The structures of some natural products early identified as medium-ring lactones were revised after total synthesis.

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“…However, it is very difficult to obtain ACPC in higher yields by reacting ACPA with thionyl chloride or phosphorous pentachloride. Literature search revealed that the suitable esters or amides were obtained by reacting carboxylic acid directly with alcohols or amines using 1-methyl-2-halopyridinium salts as a condensation reagent under mild reaction conditions in a single step with out converting the acid into corresponding acid chloride [32]. Matsukawa et al reported that the direct polycondensation method is quite preferable to prepare the macroinitiators and co-polymers [27].…”

Section: Glycidyl Azide Polymer Macroinitiator (Gapmi)mentioning

confidence: 99%

Synthesis and characterization of HTPB-GAP cross-linked co-polymers

Mohan¹,

Raju²

2005

Designed Monomers and Polymers

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Abstract-Cross-linked co-polymers containing glycidyl azide polymer (GAP) and hydroxyl-terminated poly(butadiene) (HTPB) segments have been obtained by chemical reactions. The reactions involves two steps. In the first step the GAP macroinitiator (GAPMI) is synthesized by the condensation reaction of GAP-diol with 4,4 -azobis(4-cyanopentanoic acid) (ACPA) in the presence of N-methyl-2-chloropyridinium iodide (MCPI). The GAPMI obtained is used for the cross-linking or grafting reactions with HTPB at an elevated temperature in the second step. The cross-linked co-polymers are isolated from the crude reaction mixture by fractional precipitation technique using chloroform as solvent and methanol as non-solvent. The co-polymers have been well characterized by using IR, 1 H-NMR and 13 C-NMR spectral analysis, and the molecular weights of the co-polymers have been determined by gel permeation-chromatography (GPC) and vapour pressure osmometry (VPO). The co-polymer exhibited two glass transition temperatures for HTPB-GAP co-polymer, at −74.03 • C and −35.84 • C. During the thermal analysis, the cross-linked co-polymers exhibited two exothermic peaks and one endothermic peak, indicating the presence of HTPB and GAP polymeric chain segments in the co-polymers. Further, the TGA studies revealed a four step-weight loss, suggesting the decomposition of the co-polymer is similar to that of their homo-polymers.

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A Convenient Method for the Synthesis of Carboxylic Esters

Abstract: The equimolar reactions of carboxylic acids and alcohols with 1-methyl-2-halopyridinium salts in the presence of two equimolar amounts of tri-n-butylamine afforded the corresponding carboxylic esters in good yields.

Cited by 217 publications

References 4 publications

Synthesis and plant growth-regulating activities of L-lactic acid derivatives of 4-chloroindole-3-acetic acid

Synthesis and plant growth-regulating activities of L-lactic acid derivatives of 4-chloroindole-3-acetic acid

Natural occurrence, biological activities and synthesis of eight-, nine-, and eleven-membered ring lactones

Synthesis and characterization of HTPB-GAP cross-linked co-polymers

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