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

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

Vaithiyanathan Vadivel  1 , Ravichandran Ganesan  1 , Vishnu Kannaiyan  1 , Ezhumalai Vellikannu  1 , Thirumailavan Vijayakumar  2
Affiliations

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

Vaithiyanathan Vadivel et al. ACS Omega. .

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Generality for the C–C bond cleavage using phenylhydrazine as deprotection.
Scheme 1
Scheme 1. MBH Adduct as C-3 Protection and C–C Bond Cleavage as Deprotection
Scheme 2
Scheme 2. Yield Optimization of C–C Bond Cleavage
Scheme 3
Scheme 3. Isomer Selectivity of C=N Bond Cleavage Reaction
Figure 2
Figure 2
Generality for the C=N bond cleavage reaction from the E isomer.
Figure 3
Figure 3
Pictorial justification for the protection–deprotection methodology in isatin molecules.
Figure 4
Figure 4
UV spectroscopic proof for protection–deprotection in isatin.
Figure 5
Figure 5
Generality of UV spectroscopic proof for protection–deprotection chemistry in isatins.
Scheme 4
Scheme 4. Comparitive Study on Report and Literature Method
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