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Synthesis method of divergently oriented azacycles

A nitrogen heterocyclic and divergent technology, applied in the field of metal-catalyzed carbene cyclization, can solve the problems of narrow substrate range and difficult preparation of substrates, and achieve the effects of difficult preparation, novel structure and easy operation.

Active Publication Date: 2014-12-10
山东雪地铝业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] These methods have certain limitations, such as complex substrates that are difficult to prepare, and narrow substrate ranges.

Method used

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  • Synthesis method of divergently oriented azacycles
  • Synthesis method of divergently oriented azacycles
  • Synthesis method of divergently oriented azacycles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Mix 2 mmol of 1-p-toluenesulfonyltriazole 7a and 0.01 mmol of rhodium acetate in 10 ml of toluene and stir at a temperature of 120 degrees. After 2 hours, stop heating, add 2 ml of methanol, 5 mmol of potassium carbonate and a drop of water, stirred at room temperature for 12 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography After separation and purification, the corresponding nitrogen heterocyclic aldehydes 8a and 9a were obtained (see Table 1). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

Embodiment 2

[0034] Mix 2 mmoles of 1-p-toluenesulfonyltriazole 7b and 0.1 mmoles of rhodium acetate in 10 ml of dichloroethane and stir at a temperature of 50 degrees. After 5 hours, stop heating, add 2 ml of methanol, 5 ml Molar potassium carbonate and a drop of water, stirred at room temperature for 8 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography After separation and purification, the corresponding nitrogen heterocyclic aldehydes 8b and 9b were obtained (see Table 1). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

Embodiment 3

[0036] Mix 2 mmoles of 1-p-toluenesulfonyltriazole 7c and 0.04 mmoles of rhodium acetate in 10 ml of toluene and stir at a temperature of 120°C. After 10 minutes, stop heating and add 2 ml of methanol and 5 mmoles of potassium carbonate. and a drop of water, stirred at room temperature for 12 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography After separation and purification, the corresponding nitrogen heterocyclic aldehydes 8c and 9c were obtained (see Table 1). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

[0037] Table 1. Preparation of divergent N-allyl-3-indolaldehyde and 3-azabicycl...

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Abstract

The invention discloses a synthesis method of divergently oriented azacycles and belongs to the technical field of chemical pharmaceutics and preparation of fine chemicals. By virtue of the synthesis method of divergently oriented azacycle, polysubstituted N-allyl-3-indolal and 3-diazabicyclo[3,1,0] hexanal can be synthesized at one time; sulfonyl triazole catalyzed by metal is decomposed into metal carbine, subsequently, the metal carbine is cyclized so as to efficiently obtain two types of differently structural azacycles, namely N-allyl-3-indolal and 3-diazabicyclo[3,1,0] hexanal. The invention provides a novel technical route for efficiently preparing derivatives of functionalized N-allyl-3-indolal and 3-diazabicyclo[3,1,0] hexanal derivatives. The synthesis method of divergently oriented azacycles has a wide application range in the field of chemical pharmaceutics and fine chemicals.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy and fine chemical preparation, namely divergent synthesis-oriented N-allyl-3-indolaldehyde and 3-azabicyclo[3,1,0]hexanal, especially related to metal catalysis The carbene cyclization reaction can efficiently generate two kinds of multi-substituted nitrogen heterocyclic rings, and can effectively control the relative proportion of the products. The invention provides a new technical route and design strategy for efficiently preparing functionalized nitrogen heterocyclic derivatives, and has wide applications in the fields of chemical pharmacy and fine chemical industry. Background technique [0002] Nitrogen heterocycles are a large class of important organic compounds. Many nitrogen heterocycles have special chemical and biological activities, exist in many natural products and drug molecules, and are also used in functional materials. The nitrogen heterocyclic compounds containing al...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07D209/52C07D209/14
CPCC07D209/12C07D209/14C07D209/52
Inventor 徐华栋徐科贾志宏周皓沈美华
Owner 山东雪地铝业科技有限公司
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