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利用(2,4-二硝基苯基)肼和K-10黏土作为保护-脱保护化学方法,从1,5,6-三取代异吲哚酮的MBH加合物合成取代异吲哚酮。

Synthesis of Substituted Isatins from the MBH Adduct of 1,5,6-Trisubstituted Isatins Using (2,4-Dinitrophenyl)hydrazine and K-10 Clay Explored as Protection-Deprotection Chemistry.

作者信息

Vadivel Vaithiyanathan, Ganesan Ravichandran, Kannaiyan Vishnu, Vellikannu Ezhumalai, Vijayakumar Thirumailavan

机构信息

Department of Chemistry, Arignar Anna Government Arts College, Villupuram (Re-accredited by the NAAC with "B+" and Affiliated to Thiruvalluvar University, Vellore), Villupuram, Tamil Nadu 605 602, India.

Thiruvalluvar University Post Graduate Extension Centre, Villupuram 605 602, India.

出版信息

ACS Omega. 2019 May 31;4(5):9563-9568. doi: 10.1021/acsomega.9b01002.

Abstract

An interesting synthetic transformation of protection-deprotection chemistry in an isatin molecule is achieved. Morita-Baylis-Hillman (MBH) adduct formation used as protection of the C-3 position in the isatin molecule is reported. C-C bond cleavage in the MBH adduct of isatin with the help of phenylhydrazine and C=N bond cleavage in the phenylhydrazone derivative of isatin with the help of K10 clay are studied systematically and reported as deprotection.

摘要

实现了异吲哚酮分子中保护-脱保护化学的一种有趣的合成转化。报道了将Morita-Baylis-Hillman(MBH)加合物的形成用作异吲哚酮分子中C-3位的保护。系统研究了在苯肼的帮助下异吲哚酮的MBH加合物中的C-C键断裂以及在K10黏土的帮助下异吲哚酮苯腙衍生物中的C=N键断裂,并将其报道为脱保护反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9df5/6648401/1125e116448c/ao-2019-010024_0011.jpg

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