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由茚三酮快速绿色合成新型4-甲基-1,2,5,6-四氮杂荧蒽-3(2)-酮类似物：N/S-烷基化和氮杂迈克尔加成反应

Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition.

作者信息

Boraei Ahmed T A, Ghabbour Hazem A, Sarhan Ahmed A M, Barakat Assem

机构信息

Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, Egypt.

Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.

出版信息

ACS Omega. 2020 Mar 3;5(10):5436-5442. doi: 10.1021/acsomega.0c00045. eCollection 2020 Mar 17.

DOI:10.1021/acsomega.0c00045
PMID:32201835
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7081446/
Abstract

A straightforward green synthesis of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2)-one is reported from ninhydrin via condensation with ethyl acetoacetate, followed by cyclization with hydrazine hydrate in water as a benign solvent. Tetraazafluoranthen-3-thione was obtained using Lawesson's reagent. N-alkylated tetraazafluoranthen-3-one and S-alkylated analogues were synthesized via alkylation. The investigation of the unique reactivity of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2)-one/thione toward the alkylation and aza-Michael additions was explored.

摘要

报道了一种从茚三酮出发，经与乙酰乙酸乙酯缩合，然后在作为良性溶剂的水中用水合肼环化，直接绿色合成4-甲基-1,2,5,6-四氮杂荧蒽-3(2)-酮的方法。使用劳森试剂得到四氮杂荧蒽-3-硫酮。通过烷基化合成了N-烷基化四氮杂荧蒽-3-酮和S-烷基化类似物。研究了4-甲基-1,2,5,6-四氮杂荧蒽-3(2)-酮/硫酮对烷基化和氮杂迈克尔加成的独特反应性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/e41c244e647e/ao0c00045_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/80cb1d5a9778/ao0c00045_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/537ecd4ddbff/ao0c00045_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/72cb1166b28c/ao0c00045_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/654d7df5e45a/ao0c00045_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/3778555b0dc5/ao0c00045_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/e8f63a68be8a/ao0c00045_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/188969b382a1/ao0c00045_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/7bc308f2e7a8/ao0c00045_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/09ae95f5e858/ao0c00045_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/e41c244e647e/ao0c00045_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/80cb1d5a9778/ao0c00045_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/537ecd4ddbff/ao0c00045_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/72cb1166b28c/ao0c00045_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/654d7df5e45a/ao0c00045_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/3778555b0dc5/ao0c00045_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/e8f63a68be8a/ao0c00045_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/188969b382a1/ao0c00045_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/7bc308f2e7a8/ao0c00045_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/09ae95f5e858/ao0c00045_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f348/7081446/e41c244e647e/ao0c00045_0010.jpg

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