期刊
TETRAHEDRON
卷 121, 期 -, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.132920
关键词
Phthalazines; N-hetereoarenes; C-H functionalization; Ketobenzaldehyde; Acylhydrazone; Lead tetraacetate
资金
- Thailand Science Research and Innovation (TSRI)
- Chulabhorn Research Institute [2536703/42320]
- Center of Excellence on Environmental Health and Toxicology (EHT) , OPS, Ministry of Higher Education, Science, Research and Innovation
- Faculty of Science and Technology Thammasat University [TB 06/2018]
This article describes an improved synthetic strategy for synthesizing 1-substituted 4-H phthalazines under mild conditions. The method has high practical value and can be used to synthesize various analogs.
An improved synthetic strategy for 1-substituted 4-H phthalazines using a convenient, three-step re-action sequence under mild conditions is described. The protocol involves condensation of hydrazine hydrate with o-ketobenzaldehydes derived through the Pb(OAc)(4) oxidation of the N-acylhydrazones of salicylaldehydes. This pathway is of high practical value since a wide variety of substituted acylhy-drazides and salicylaldehydes, the substrates for N-acylhydrazones, are commercially available. In addition, the three-step sequence could be scaled up without the need for intermediate purification affording a broad range of products in high yield. 1-Phenyl 4-H phthalazine was a versatile compound providing ready access to multiple phthalazine analogs, including the vasodilating agent MY5445. (C) 2022 Elsevier Ltd. All rights reserved.
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