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Preparation method of isoquinoline-1-formamide compounds

A technology of carboxamides and isoquinoline, which is applied in the field of preparation of isoquinoline-1-carboxamide compounds, can solve the problems that the reaction conditions need to be improved, the reaction cost increases metal waste and the like

Inactive Publication Date: 2021-07-06
HUBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of reaction traditionally uses Cu or Pd as a catalyst, and at the same time, one or more expensive metals are used as auxiliary reagents in the catalytic system, and the reaction conditions will increase the reaction cost and produce a large amount of of metal waste
With the strengthening of people's awareness of environmental protection and the current development trend of green, efficient and economical chemical reactions, the reaction conditions of this type of reaction need to be improved.

Method used

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  • Preparation method of isoquinoline-1-formamide compounds
  • Preparation method of isoquinoline-1-formamide compounds
  • Preparation method of isoquinoline-1-formamide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1, the preparation of N-tert-butyl-isoquinoline-1-carboxamide (C-a):

[0024]

[0025] Add 0.4mmol oxidant (Na 2 S 2 o 8 ), 0.2mmol isoquinoline, 0.6mmol tert-butyl isocyanide, 2mL acetonitrile solution and a No. 5 magnet. Pass the condensed water through the condenser pipe from bottom to top, and then place the reactor in an oil bath at 120° C. for heating for 24 hours. Add 15mL of water, and extract three times with 10mL of ethyl acetate each time, the obtained organic phases are combined, spin-dried by a rotary evaporator, and the crude product is separated and purified by column chromatography to obtain N-tert-butyl-isoquinoline-1-carboxamide ( C-a) 34.2 mg as a white solid, 75% yield.

[0026] H NMR 1 H NMR (400MHz, CDCl 3 ):δ1.54(s,9H),7.61-7.69(m,2H),7.73(d,J=5.52Hz,1H),7.78-7.81(m,1H),8.09(s,1H),8.40( d,J=5.56Hz,1H),9.58-9.55(m,1H),; 13 C NMR (100MHz, CDCl 3 ): δ27.7, 50.1, 123.0, 125.7, 125.8, 127.0, 127.3, 129.3, 136.3, 138.9, 148.3, 164...

Embodiment 2

[0027] Embodiment 2, the preparation of N-tert-butyl-phenanthridine-6-carboxamide (C-b)

[0028]

[0029] Add 0.4mmol oxidant (Na 2 S 2 o 8 ), 0.2mmol phenanthridine, 0.6mmol tert-butyl isocyanide, 2mL acetonitrile solution and a No. 5 magnet. Pass the condensed water through the condenser pipe from bottom to top, and then place the reactor in an oil bath at 120° C. for heating for 24 hours. Add 15mL of water, extract three times with 10mL ethyl acetate each time, the organic phases obtained are combined, spin-dried by a rotary evaporator, and the crude product is separated and purified by column chromatography to obtain N-tert-butyl-phenanthridine-6-carboxamide (C-b )36.8mg, a colorless oily liquid, the yield was 67%.

[0030] H NMR 1 H NMR (400MHz, CDCl 3 ):δ1.60(s,9H),7.75-7.68(m,3H),7.84(t,J=7.62Hz,1H),8.07(s,1H),8.15(d,J=7.78Hz,1H) ,8.57(dd,J=21.6Hz,J=8.1Hz,2H),9.59(d,J=8.39Hz,1H); 13 C NMR (100MHz, CDCl 3 ): δ28.8, 51.3, 121.7, 122.1, 124.3, 125.4, 127.8, 128...

Embodiment 3

[0031] Embodiment 3, the preparation of N-tert-butyl-3-methylisoquinoline-1-carboxamide (C-c)

[0032]

[0033] Add 0.4mmol oxidant (Na 2 S 2 o 8 ), 0.2mmol 3-methylisoquinoline, 0.6mmol tert-butyl isocyanide, 2mL acetonitrile solution and a No. 5 magnet. Pass the condensed water through the condenser pipe from bottom to top, and then place the reactor in an oil bath at 120° C. for heating for 24 hours. Add 15 mL of water, extract three times with 10 mL of ethyl acetate each time, combine the obtained organic phases, spin dry by rotary evaporator, and separate and purify the crude product by column chromatography to obtain N-tert-butyl-3-methylisoquinoline-1 - Formamide (C-c) 31.8 mg, a colorless oily liquid, yield 66%.

[0034] H NMR 1 H NMR (400MHz, CDCl 3 ):δ1.54(s,9H),2.88(s,3H),7.58-7.54(m,2H),7.65-7.61(m,1H),7.72(d,J=8.15Hz,1H),8.22( s,1H),9.56(d,J=8.8Hz,1H); 13 CNMR (100MHz, CDCl 3 ): δ25.3, 28.9, 52.7, 119.1, 121.2, 126.4, 127.6, 127.9, 135.8, 143.2, 148.6,...

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Abstract

The invention relates to a preparation method of isoquinoline-1-formamide compounds. The preparation method comprises the following steps: mixing an oxidant, a reactant I, a reactant II and a solvent in a reactor, carrying out amidation reaction, and separating and purifying after the reaction to obtain the isoquinoline-1-formamide compounds, wherein the oxidizant is persulfate; the reactant I is an isoquinoline compound; and the reactant II is optionally selected from tert-butyl isocyanide, phenyl isocyanide and cyclohexyl isocyanide. The method is mild in reaction condition, high in selectivity, relatively high in yield and environment-friendly. Through detection, the synthesized isoquinoline-1-formamide compounds have certain biological activity and can be applied to the fields of drug synthesis, pesticide synthesis, paint and dye synthesis and the like.

Description

technical field [0001] The invention relates to a method for preparing amide compounds mediated by persulfate radicals, in particular to a method for preparing isoquinoline-1-carboxamide compounds. Background technique [0002] Amide compounds are important chemical intermediates and products, which are widely used in medicine, pesticides, coatings, dyes and other fields. Amide compounds widely exist in nature, and many alkaloids (such as colchicine, halosine, and ergot alkaloid, etc.) and drugs (atorvastatin, lisinopril, and diltiazem, etc.) contain amide structural units. The universal application of amide compounds has aroused great interest of scientific researchers, making research in this field one of the current research hotspots. [0003] The construction of carbon-carbon (C-C) bonds is an unavoidable theme in the neighborhood of organic chemistry, and the activation of inert bonds greatly improves atom economy and environmental friendliness by distinguishing from t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/26C07D221/12
CPCC07D217/26C07D221/12
Inventor 李栋周仲张谦
Owner HUBEI UNIV OF TECH