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CN-122010957-A - Preparation method of fullerene pyrrolidine quinazolinone

CN122010957ACN 122010957 ACN122010957 ACN 122010957ACN-122010957-A

Abstract

The invention discloses a preparation method of fullerene pyrrolidine quinazolinone, which belongs to the technical field of organic synthesis, namely the field of fullerene derivative synthesis, and specifically comprises the steps of taking fullerene, a 2-aminobenzamide compound and an aldehyde compound as reaction substrates, taking lead acetate and DMAP as accelerators, taking o-dichlorobenzene as a solvent, and carrying out one-step thermal reaction in air to obtain a target product fullerene pyrrolidine quinazolinone. The method has simple steps, and the obtained fullerene pyrrolidine quinazoline ketone derivatives have novel structures, greatly enrich the types of the fullerene derivatives, and have good substrate universality and wide application prospects.

Inventors

  • LI FABAO
  • LI YANAN

Assignees

  • 湖北大学

Dates

Publication Date
20260512
Application Date
20251219

Claims (9)

  1. 1. A process for preparing fullerene-pyrrolidine-quinazoline ketone includes such steps as heating fullerene, 2-aminobenzamide compound and aldehyde compound as raw materials, lead acetate and DMAP as promoter, o-dichlorobenzene as solvent in air, reacting with aldehyde amine, and synthesizing fullerene-pyrrolidine-quinazoline ketone ; Wherein the 2-aminobenzamide compound is 2-aminobenzamide or a derivative thereof with a substituent R 1 substituted on a benzene ring, and the substituent R 1 is one of alkyl, halogenated group and alkoxy; The aldehyde compound has A structure wherein R 2 is one of alkyl and benzyl; The fullerene is C 60 fullerene.
  2. 2. The method for preparing fullerene-pyrrolidine-quinazolinone according to claim 1, wherein the synthesis equation is as follows: 。
  3. 3. The method for preparing fullerene-pyrrolidine-quinazolinone according to claim 2, wherein said 2-aminobenzamide compound is 2-aminobenzamide, and said aldehyde compound is n-propanal, n-butanal, n-pentanal and phenylpropionaldehyde.
  4. 4. The method for preparing fullerene pyrrolidine quinazolinone according to claim 2, wherein the aldehyde compound is n-propionaldehyde, and the 2-aminobenzamide compound is 2-amino-5-methylbenzamide, 2-amino-5-methoxybenzamide, 2-amino-5-fluoro-benzamide, 2-amino-5-chloro-benzamide and 2-amino-5-bromo-benzamide.
  5. 5. A process for the preparation of a fullerene-pyrroloquinazolinone according to any of claims 1 to 4, comprising the steps of: Adding raw materials of fullerene C 60 , 2-aminobenzamide compounds and aldehydes compounds into a reaction container, adding lead acetate and DMAP as accelerators, adding solvent o-dichlorobenzene, fully dissolving under an ultrasonic instrument, then heating and stirring the reaction container on a constant temperature heater, after the reaction is finished, cooling the reaction liquid to room temperature, then adding the reaction liquid into a silica gel column for separation, taking carbon disulfide as an eluent, firstly obtaining unreacted fullerene, and then using carbon disulfide and dichloromethane as the eluent for continuous separation, thus obtaining the brown solid fullerene pyrrolidine quinazolinone derivative.
  6. 6. The preparation method of claim 5, wherein the constant-temperature heating temperature is 170 ℃, and the feeding molar ratio of the fullerene, the 2-aminobenzamide compound to the aldehyde compound to the lead acetate to the DMAP is 1:2-8:2-8:1-8:0.5-2.
  7. 7. A fullerene-pyrroloquinazolinone prepared by the method of claim 6, wherein the fullerene-pyrroloquinazolinone has the structural formula of Wherein R 1 is one of alkyl, halogeno and alkoxy, R 2 is one of alkyl and benzyl, and the fullerene is C 60 fullerene.
  8. 8. A fullerene-pyrroloquinazolinone prepared by the method of claim 7, wherein the fullerene-pyrroloquinazolinone comprises one of the following compounds: 。
  9. 9. Use of the fullerene pyrrolidone of claim 8 for the preparation of perovskite solar cell electron transport materials.

Description

Preparation method of fullerene pyrrolidine quinazolinone Technical Field The invention belongs to the technical field of organic synthesis, and particularly relates to a method for preparing fullerene pyrrolidine quinazolinone based on lead acetate promotion. Background The unique three-dimensional all-carbon hollow molecular structure and photoelectric property of fullerene are of great interest in the fields of material science, biomedicine, supermolecular chemistry, organic photovoltaic and perovskite solar cells and the like. The fullerene skeleton is chemically modified, and a functional fullerene system is constructed by accessing diversified functional groups, so that the method has become one of the core directions of fullerene research. As shown in formula 1, 2018, the group of professor Wang Guanwu of the university of science and technology reported that C 60 and hydrazide compound undergo cycloaddition reaction to synthesize a novel fullerene tetrahydropyridazine compound under the promotion of Cu (OAc) 2·H2 O. The mechanism studies showed that the formation of the resulting product was dominated by the hetero Diels-Alder process (Organic Chemistry Frontiers, 2018, 5:1188-1193). Formula 1. As shown in formula 2, 2019, wang Guanwu taught that the subject group also produced 2-arylvinyl substituted [60] fullerene pyrrolidines by reaction of triethylamine and aromatic aldehydes with C 60 (European Journal of Organic Chemistry, 2019, 2019: 6504-6509). Formula 2. As shown in formula 3, 2021, henan university Liu Tong, committee describes the first metal-free catalyzed [60] fullerene multicomponent cyclization reaction. C 60, ketones and indoles are cyclized by [2+2+2] with I 2 as a catalyst to give a series of fullerene-1, 2-tetrahydrocarbazole derivatives (Organic Letters, 2021, 23:1775-1781). Formula 3. As shown in formula 4, 2023, professor Li Fabao, university of lake north, reported that ketone group-containing [60] fullerene pyrrolidine, N-unsubstituted [60] fullerene pyrrolidine and paraformaldehyde undergo an aminomethylation reaction under the acceleration of tsoh·h 2 O to successfully synthesize ketone group-containing [60] fullerene pyrrolidine dimer derivatives (Organic & Biomolecular Chemistry, 2023, 21:4881-4892). Formula 4. CN120623098a discloses a fullerene pyrrolidine derivative as an electron transport layer material, which significantly improves the photoelectric performance and stability of tin-based perovskite solar cells. The PCE of the device prepared by the F6/F12 composite material is as high as 12.0 percent. In addition, the derivatives also show excellent chemical stability and environmental adaptability, effectively prolong the service life of devices and provide powerful support for commercialization of tin-based perovskite solar cells. Through the current report, the novel fullerene pyrrolidine derivative material has great potential and prospect in the perovskite field, and we need to think about more effective synthesis strategies to prepare different fullerene pyrrolidine derivatives so as to widen the application market. Disclosure of Invention The invention aims to solve the technical problems of overcoming the defects of the prior art, providing a synthetic method for promoting fullerene pyrrolidine quinazoline ketone based on lead acetate, and verifying substrate universality. The invention adopts the following technical scheme to realize the aim, and the preparation method of the fullerene pyrrolidine quinazolinone is characterized in that fullerene, a 2-aminobenzamide compound and an aldehyde compound are used as raw materials, lead acetate and DMAP are used as accelerators, o-dichlorobenzene is used as a solvent, and the materials are heated in air to generate aldehyde-amine reaction to synthesize the fullerene pyrrolidine quinazolinone; Wherein the 2-aminobenzamide compound is 2-aminobenzamide or a derivative thereof with a substituent R 1 substituted on a benzene ring, and the substituent R 1 is one of alkyl, halogenated group and alkoxy; The aldehyde compound has A structure wherein R 2 is one of alkyl and benzyl; The fullerene is C 60 fullerene. Further, the synthesis equation of the aldehyde amine reaction is as follows: 。 further, the 2-aminobenzamide compound is 2-aminobenzamide, and the aldehyde compound is n-propionaldehyde, n-butyraldehyde, n-valeraldehyde and phenylpropionaldehyde. Further, the aldehyde compound is n-propionaldehyde, and the 2-aminobenzamide compound is 2-amino-5-methylbenzamide, 2-amino-5-methoxybenzamide, 2-amino-5-fluoro-benzamide, 2-amino-5-chloro-benzamide and 2-amino-5-bromo-benzamide. The invention also provides a preparation method of the fullerene pyrrolidine quinazolinone, which comprises the following specific steps: Adding raw materials of fullerene C 60, 2-aminobenzamide compounds and aldehydes compounds into a reaction container, adding lead acetate and DMAP as accelerators, adding solvent o-dichlorobenzene, fully diss