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A kind of synthetic method of o-iodo α-acyloxycarbonyl compound

A technique for the synthesis of acyloxycarbonyl groups, which is applied in the field of chemical synthesis, can solve problems such as excess, low yield, and harsh reaction conditions, and achieve the effects of simple operation, good yield, and mild reaction conditions

Inactive Publication Date: 2019-06-04
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the reported reactions suffer from certain disadvantages, such as the need to use excess ketones, excess potentially dangerous peroxide oxidizing agents, toxic metal catalysts, harsh reaction conditions, and low yields.

Method used

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  • A kind of synthetic method of o-iodo α-acyloxycarbonyl compound
  • A kind of synthetic method of o-iodo α-acyloxycarbonyl compound
  • A kind of synthetic method of o-iodo α-acyloxycarbonyl compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Compound A1

[0027]

[0028] Ethyl acetate / petroleum ether=1, 11, v / v; white solid, yield: 90%; 1 H NMR (400 MHz, Chloroform- d ) δ: 8.11-8.00 (m, 2H), 7.97 (d, J = 7.4 Hz, 2H), 7.63 (t, J =7.4 Hz, 1H), 7.51 (t, J = 7.7 Hz, 2H), 7.45 (t, J =7.6 Hz, 1H), 7.19 (td, J =7.8, 1.6 Hz, 1H), 5.60 (s, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ: 191.7, 165.8, 141.4, 134.2, 134.1, 134.0, 133.1, 131.7, 128.9, 128.0, 127.83, 94.5, 66.7.

Embodiment 2

[0029] Example 2 Compound A2

[0030]

[0031] Ethyl acetate / petroleum ether=1: 15, v / v; white solid, yield; 86%; 1 H NMR (400 MHz, Chloroform- d ) δ: 8.04 (ddd, J = 15.3, 7.9, 1.3 Hz, 2H), 7.86 (d, J = 8.2 Hz,2H), 7.45 (td, J = 7.6, 1.0 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.19 (td, J =7.7, 1.7 Hz, 1H), 5.57 (s, 2H), 2.43 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ:191.3, 165.8, 145.0, 141.4, 134.2, 133.0, 131.7, 131.7, 129.6, 128.0, 127.9,94.4, 66.7, 21.8. HRMS (ESI) exact mass calculated for C 16 h 13 IO 3 [M+Na] + :402.9802, found: 402.9804; IR (neat): ν max (cm -1 ) = 3063, 2988, 1729, 1693, 1103, 1016, 742, 699.

Embodiment 3

[0032] Example 3 Compound A3

[0033]

[0034] Ethyl acetate / petroleum ether=1: 11, v / v; white solid, yield: 81%; 1 H NMR (400 MHz, Chloroform- d ) δ: 7.96 (d, J = 7.9 Hz, 2H), 7.87 (s, 2H), 7.61 (d, J = 7.1 Hz,1H), 7.50 (t, J = 6.9 Hz, 2H), 7.01 (d, J = 7.9 Hz, 1H), 5.59 (s, 2H), 2.35(s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ: 191.8, 165.9, 141.1, 138.2, 134.2, 134.1, 134.0, 133.8, 132.4, 128.9, 127.8, 90.4, 66.7, 20.9. HRMS (ESI) exact masscalculated for C 16 h 13 IO 3 [M+Na] + : 402.9802, found: 402.9805; IR (neat): ν max (cm -1 ) = 3053, 2990, 1718, 1687, 1301, 1273, 1114, 700.

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Abstract

The invention provides a synthesis method of an o-iodo-alpha-acyloxycarbonyl compound. The o-iodo-alpha-acyloxycarbonyl compound is synthesized under the catalysis of N-heterocyclic carbene precursor salt with an EBX reagent as a raw material and a mixed solution of an organic solvent and water as a solvent. Compared with existing methods, the method has a wide applicable substrate range, adopts mild reaction conditions and is simple and convenient to operate and high in reaction efficiency.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a method for synthesizing o-iodo α-acyloxycarbonyl compounds by catalyzing EBX reagents with N-heterocyclic carbene. Background technique [0002] Ortho-iodo α-acyloxycarbonyl compounds are important structural units in organic synthetic chemistry, widely exist in biologically active natural products, and are common synthetic drug structural units. Since the 1970s, the synthesis and research of ortho-iodo α-acyloxycarbonyl compounds have attracted widespread attention in the chemical community. Previously, o-iodo α-acyloxycarbonyl compounds were prepared by coupling reactions of α-halogenated carbonyl compounds or α-diazo ketones with basic carboxylates and ketones under the action of heavy metal oxidants. It was subsequently found that supervalue iodine compounds can act as effective oxidizing agents to promote acyloxylation reactions. In recent years, EB...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/12C07B41/06C07C67/00C07C69/78C07C253/30C07C255/56C07C201/12C07C205/45C07C205/58C07D333/22C07D213/50
CPCC07B41/06C07B41/12C07C67/00C07C69/78C07C201/12C07C205/45C07C205/58C07C253/30C07C255/56C07D213/50C07D333/22
Inventor 李毅王亚洲
Owner FUZHOU UNIV