Regioselective addition of Grignard reagents to 2,6-dicyanoanilines and cyclization to new quinazoline derivatives under thermal/microwave irradiation conditions

Maitraie, D.; Yakaiah, T.; Srinivas, K.; Reddy, G. Venkat; Ravikanth, S.; Narsaiah, B.; Rao, P. Shanthan; Ravikumar, K.; Sridhar, B.

doi:10.1016/j.jfluchem.2006.01.003

Cited by 15 publications

(8 citation statements)

References 20 publications

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“…A useful strategy to synthesize new quinazoline derivatives was developed by Maitraie et al (2006). 2,6-Dicyanoaniline derivatives 16 on the reaction with Grignard reagents produced imine regioisomers 17 and 18, which, after separation and identification, reacted with various aldehydes under MWI with 450 W to provide novel quinazolines 19 and 20, respectively.…”

Section: Benzaldehydesmentioning

confidence: 99%

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

Mohammadkhani

Heravi

2020

Front. Chem.

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Microwave irradiation (MWI), as a unique, effective, sustainable, more economic, and greener source of energy compared to conventional heating, is applied in different organic transformations to result in the rapid formation of desired compounds due to thermal/kinetic effects. In this review, we try to underscore the applications of microwave irradiation (MWI) in the synthesis of quinazoline and quinazolinone derivatives that have been achieved and reported on in the last two decades.

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Section: Benzaldehydesmentioning

confidence: 99%

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

Mohammadkhani

Heravi

2020

Front. Chem.

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“…Studying the regioselective addition of Grignard reagents to 2,6-dicyanoanilines, Narsaiah and co-workers [15] described the microwave-assisted cyclization of the intermediate imines to provide in good yields novel 2,4-disubstituted quinazolines with various groups on the benzenic part of the aromatic core. In this paper, the method describes 4-9 min of irradiation at a power input of 450 W in sealed tubes.…”

Section: 4-di-substituted Quinazolinesmentioning

confidence: 99%

Microwave-Assisted Synthesis of Bioactive Quinazolines and Quinazolinones

Besson¹,

Chosson

2007

CCHTS

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This paper aims to review recent developments in the synthesis of quinazolines and quinazolinone derivatives under conditions that include the application of microwave heating in the ring forming step. Recently, two reviews on the synthesis and chemistry of natural and synthetic quinazolines and quinazolinones have been published. This review highlights significant examples where microwave heating has been either synthetically enabling or has provided a key advantage over conventional thermal methods. Wherever possible, this review will focus on chemistry carried out using monomode systems and well-designed type of instrumentation. The review is grouped according to the main heterocycle types in order of increasing complexity; commencing with quinazolines and their derivatives. The microwave-assisted synthesis of quinazolines and quinazolinones will be classified and based on the substitution patterns of the ring system. Syntheses of heterocyclic systems of particular biological or commercial interest are emphasized.

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“…Many quinazoline derivatives have been synthesized using various methods, such as solid‐phase , microwaves , cyclization , oxidation , and One‐pot synthesis with different starting materials, such as anthranilic acid, 2‐aminobenzonitrile, 2‐nitrobenzoic acid, anthranilamide, and so on. Although quninazoline derivatives have been synthesized successfully, photochemical method utilized for the synthesis of quinazoline derivatives has not been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of Novel 4‐Arylamino‐2‐phenyl‐6‐substituted‐quinazoline

Zhang

2012

Journal of Heterocyclic Chem

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Regioselective addition of Grignard reagents to 2,6-dicyanoanilines and cyclization to new quinazoline derivatives under thermal/microwave irradiation conditions

Cited by 15 publications

References 20 publications

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

Microwave-Assisted Synthesis of Bioactive Quinazolines and Quinazolinones

Synthesis and Structure of Novel 4‐Arylamino‐2‐phenyl‐6‐substituted‐quinazoline

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