Synthesis of heterocyclic compounds based on isatin through 1,3-dipolar cycloaddition reactions

Negar Lashgari,Ghodsi Mohammadi Ziarani,Viktor V Zhdankin

doi:10.3998/ark.5550190.0013.108

Negar Lashgari, Ghodsi Mohammadi Ziarani + Show 1 more

Open Access

https://doi.org/10.3998/ark.5550190.0013.108

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Journal: Arkivoc	Publication Date: May 20, 2012
Citations: 124	License type: cc-by

Abstract

This review gives an overview of the advances in the use of isatin in the synthesis of various heterocyclic compounds via 1,3-dipolar cycloaddition reactions during the period from 2000 to 2011.

Highlights

H NC N NCA multicomponent [3+2] cycloaddition reactions of 3-cyanoacetylindoles 62, aldehydes 57, isatin 1 and amino acids 6 and 17 was reported by Xu and coworkers (Scheme 19).[33]
Isatins with their multifunctionality and diversity of transformations are synthetically versatile substrates and many efforts have been made toward the synthesis of these compounds
1,3-Dipolar cycloaddition, known as the Huisgen reaction,[13] is regarded as one of the most attractive methods for the formation of pharmacologically important five-membered Nheterocyclic compounds. 1,3-Dipolar cycloaddition of ylidic species such as azomethine ylides with dipolarophiles provides an efficient and convergent approach for constructing pyrrolidine rings which are classes of compounds with significant biological activities

Summary

H NC N NC

A multicomponent [3+2] cycloaddition reactions of 3-cyanoacetylindoles 62, aldehydes 57, isatin 1 and amino acids 6 and 17 was reported by Xu and coworkers (Scheme 19).[33]. 3,5-Bis(arylmethylidene)-N-methyl-4-piperidinone 82 in reaction with isatin and benzyl amine yielded the desired product that was subsequently reacted with a nitrile oxide generated in situ from 4-chlorobenzohydroximoyl chloride and triethylamine, with a view to obtaining trispiro-compounds 86. 3,5-Bis(arylmethylidene)-N-methyl-4-piperidinone 82 in reaction with isatin and benzyl amine yielded the desired product that was subsequently reacted with a nitrile oxide generated in situ from 4-chlorobenzohydroximoyl chloride and triethylamine, with a view to obtaining trispiro-compounds This reaction furnished solely monospiroisoxazolines 87 in 45– 56% yields (Scheme 25).[39]. The multicomponent reaction of isatin 1, 3-phenyl-5-isoxazolone 88, and sarcosine 17 or Lproline 6 in methanol under reflux has been reported (Scheme 26).[40] The reaction proceeded through an unusual mechanistic pathway resulting in the synthesis of spirooxindole derivatives

H N CO2H H

H H H Ar O

Synthesis of Trispiroheterocycles

Findings

Synthesis of Tetraspiroheterocycles