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Synthesis method of lactone-lactam polycyclic compound

A technology of polycyclic compounds and synthetic methods, which is applied in the field of synthesis of lactone and lactam polycyclic compounds, can solve the problems that it is difficult to form butyrolactam units at the same time and has not been developed, and achieve a good substrate adaptability, good Effects of diastereoselectivity, mild and simple reaction conditions

Pending Publication Date: 2022-02-01
INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few subsequent reports have used this inventive strategy in the synthesis
According to existing research results, it is difficult to simultaneously form butyrolactam units while constructing butyrolactone
Thus, the synthesis of lactam-containing polysubstituted bicyclobutyrolactones remains unexplored and continues to represent a challenging area of ​​research

Method used

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  • Synthesis method of lactone-lactam polycyclic compound
  • Synthesis method of lactone-lactam polycyclic compound
  • Synthesis method of lactone-lactam polycyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-24

[0033] Embodiment 1-24 reaction condition optimization test

[0034] Using the α-benzoyl-N-phenylcarboxamide shown in formula 1a and the α-angelica lactone shown in formula 2 as templates, the effects of different solvents, catalysts and other conditions on the yield of the target product, non- The impact of enantioselectivity, the results are shown in Table 1, and the reaction formula is as follows:

[0035]

[0036] Table 1:

[0037] Example catalyst solvent Yield(%) b

dr c

1 Pyrrolidine THF 6 >20:1 2 Et 3 N

THF 13 >20:1 3 DBACO THF 11 7:1 4 DMAP THF 23 4:1 5 DBU THF 64 11:1 6 TMG THF 73 16:1 7 KOAc THF 27 >20:1 8 t-BuOK THF 53 >20:1 9 TMG DCM 69 >20:1 10 TMG EA 46 >20:1 11 TMG CH 3 CN

62 5:1 12 TMG DMF 42 2:1 13 TMG DMSO 48 2:1 14 TMG toluene 57 >20:1 15 TMG dioxane 83 >20:1 16 TMG Me...

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Abstract

The invention discloses a novel synthesis method of a lactone-lactam polycyclic compound. The novel synthesis method is characterized in that alpha-angelica lactone and a ketone amide compound are directly subjected to aldol addition and aza-Michael reaction to synthesize tetrahydro-2H-furo[3,2-b]pyrrole-2,2-5(3H)-dione skeleton compound with good yield and high diastereoselectivity under mild conditions. In addition, the above reaction is the first aldol addition / aza-Michael tandem reaction.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, in particular to a method for synthesizing a lactone-lactam polycyclic compound. Background technique [0002] Lactones and lactam derivatives are ubiquitous structural units in natural products and bioactive molecules (see formula 1), thus attracting great attention from medicinal chemists. However, developing an organic synthetic route to highly functionalized polysubstituted butyrolactones and butyrolactams to provide pharmaceutical compounds, especially butyrolactones and butyrolactams containing quaternary carbon centers, is very difficult. Importantly, the structure of multi-substituted bicyclic γ-lactone derivatives with γ-lactam backbone is the basic skeleton structure of antibiotic CJ-16,264 and its derivatives, which exhibit strong antibacterial properties and cytotoxicity. [0003] Formula 1: [0004] [0005] As one of the most efficient synthetic means to construct t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048
CPCC07D491/048
Inventor 刘洪鑫黄维蒋丽琼蒋佳慧吴超飞
Owner INST OF NEW MATERIALS & IND TECH WENZHOU UNIV