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通过控制IBX的反应活性实现喹唑啉-4(3)-酮的机械化学合成

The mechanochemical synthesis of quinazolin-4(3)-ones by controlling the reactivity of IBX.

作者信息

Alam Md Toufique, Maiti Saikat, Mal Prasenjit

机构信息

School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar, PO Bhimpur-Padanpur, Via Jatni, District Khurda, Odisha 752050, India; Tel: +919439613856.

出版信息

Beilstein J Org Chem. 2018 Sep 12;14:2396-2403. doi: 10.3762/bjoc.14.216. eCollection 2018.

DOI:10.3762/bjoc.14.216
PMID:30254705
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6142747/
Abstract

Performing any synthesis using several arylamines and hypervalent iodine(V) reagents by direct mixing is unrealistic because of the high exothermic reaction or explosion. Herein we demonstrate, when anilines were substituted with an amide group at the -position, successful chemical reactions could be performed due to intramolecular control. At maximum contact of the reacting substances, i.e. under solvent-free mechanochemical conditions, 2-aminobenzamides, aryl-, alkylaldehydes and the iodine(V) reagent -iodoxybenzoic acid (IBX) led to substituted quinazolin-4(3)-one derivatives in fair yields.

摘要

由于反应放热高或有爆炸风险，通过直接混合使用几种芳胺和高价碘（V）试剂进行任何合成都是不切实际的。在此我们证明，当苯胺在α-位被酰胺基取代时，由于分子内控制，可以成功进行化学反应。在反应物质最大程度接触时，即在无溶剂机械化学条件下，2-氨基苯甲酰胺、芳基醛、烷基醛和碘（V）试剂——亚碘酰苯甲酸（IBX）反应可得到产率尚可的取代喹唑啉-4(3)-酮衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/e2e4ce5c4d91/Beilstein_J_Org_Chem-14-2396-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/500eaaeb33d5/Beilstein_J_Org_Chem-14-2396-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/1fdc28280b8d/Beilstein_J_Org_Chem-14-2396-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/dc9d32f000c6/Beilstein_J_Org_Chem-14-2396-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/8879434cd1bd/Beilstein_J_Org_Chem-14-2396-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/2c5f64240894/Beilstein_J_Org_Chem-14-2396-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/4755dba0bf51/Beilstein_J_Org_Chem-14-2396-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/e2e4ce5c4d91/Beilstein_J_Org_Chem-14-2396-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/500eaaeb33d5/Beilstein_J_Org_Chem-14-2396-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/1fdc28280b8d/Beilstein_J_Org_Chem-14-2396-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/dc9d32f000c6/Beilstein_J_Org_Chem-14-2396-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/8879434cd1bd/Beilstein_J_Org_Chem-14-2396-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/2c5f64240894/Beilstein_J_Org_Chem-14-2396-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/4755dba0bf51/Beilstein_J_Org_Chem-14-2396-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ffe5/6142747/e2e4ce5c4d91/Beilstein_J_Org_Chem-14-2396-g008.jpg

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