A Facile and Convenient Synthetic Method for Fluorine-containing 1,2-Dihydropyrido[3,2-h]quinazolines and Pyrido[3,2-h]quinazolines

The present review focuses on the synthesis and biological evaluation of polycyclic 4(3H)-quinazolinones containing fused aromatic or heteroaromatic rings. The first part of the review is related to compounds with ring fused to the pyrimidine part of the quinazoline core. Most of the quinazolinone alkaloids belong to this class of molecules. The second part presents molecules bearing extra ring(s) fused to the benzo moiety of the quinazolinone skeleton. Their structural diversity opens new fields in the search of active molecules.

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“…Quinazolinones with a fused pyridine ring (143) have been reported earlier by Okada (Fig. 43) [136].…”

Section: Recent Advances In Synthetic Methodologiesmentioning

confidence: 59%

Survey of Recent Literature Related to the Biologically Active 4(3H)-Quinazolinones Containing Fused Heterocycles

Demeunynck¹,

Baussanne

2013

CMC

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“…Therefore, the construction of these heterocycles has received much attention in recent years. The known methods for the synthesis of pyridoquinazoline are via three steps from simple aromatic amines involving the intramolecular cyclization of benzoyl arylguanidines , or by the reaction of 2‐chloro‐4,6‐dimethylpyridine‐3‐carbonitrile with anthranilic acid , or by the condensation of chalcones with 2‐aminopyridine , or using 5,7‐bis(trifluoroacetyl)‐8‐quinolylamine as reactant to react with various aldehydes in the presence of ammonia , or some other multistep reactions .…”

Section: Introductionmentioning

confidence: 99%

A Green Synthesis of Pyrido[1,2‐a]quinazoline‐1,6‐dione Derivatives in Ionic Liquid Catalyzed by Iodine

Zhang

Wang

2014

Journal of Heterocyclic Chem

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“…Thus, the facile synthetic method for pyrido [3,2-h]quinazolines 3, 4 from 2, using aldehydes and ammonia was found (Scheme 1). 6 In a continuation of this work, we have investigated the reaction of 2 with ketones instead of aldehydes, in the presence of ammonia, with the aim of synthesizing the desired fluorine-containing 1,10-phenanthrolines 5a−h. The results are shown in Scheme 2 and summarized in Table 1.…”

mentioning

confidence: 99%

“…It is noteworthy that the pyrido [3,2-h]quinazoline derivative, like 3, was not formed at all, in contrast to the reaction of 2 with aldehydes. 6 Similarly, 2-ethyl-3-methyl derivative 5b was also prepared quantitatively by the reaction of 2 with 3-pentanone under slightly forced conditions. Next, we attempted to carry out the reaction of 2 with cyclic ketones in order to synthesize 1,10-phenanthrolines fused by a cycloalkane ring.…”

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confidence: 99%

A Simple and Efficient Synthetic Method for Fluorine-Containing 1,10-Phenanthrolines

Okada¹,

Tsukushi²

2000

Synthesis

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Various fluorine-containing 1,10-phenanthrolines were synthesized in excellent yields by the reaction of 5,7-bis(trifluoroacetyl)-8-quinolylamine with ketones in the presence of aqueous ammonia.1,10-Phenanthroline and the related derivatives are important heterocyclic systems because of being applicable to important chelating ligands forming stable complexes with transition metals. 1 Furthermore, some of these complexes have been useful in studies of not only the novel catalysts 2 such as phase-transfer and asymmetric ones but also the DNA binding properties which can be expected to develop novel probes of nucleic acid structure and function. 3 Besides, much attention in recent years has been focused on the development of new methodologies for the syntheses of many kinds of fluorine-containing heterocycles, since these compounds are now widely recognized as important organic materials showing specific functions as well as interesting biological activities. 4Recently, we have reported that N,N-dimethyl-5,7-bis(trifluoroacetyl)-8-quinolylamine 1 undergoes a novel aromatic nucleophilic substitution with amines under mild conditions to give the corresponding 5,7-bis(trifluoroacetyl)-8-quinolylamines in excellent yields. 5 Moreover, we have set about the investigations on utilization of 5,7-bis(trifluoroacetyl)-8-quinolylamine 2, which can be easily prepared by the Me 2 N-NH 2 exchange reaction of 1 with ammonia, 5 as a new and convenient building block for construction of CF 3 -containing heterocycles having a quinoline skeleton. Thus, the facile synthetic method for pyrido[3,2-h]quinazolines 3, 4 from 2, using aldehydes and ammonia was found (Scheme 1). 6 In a continuation of this work, we have investigated the reaction of 2 with ketones instead of aldehydes, in the presence of ammonia, with the aim of synthesizing the desired fluorine-containing 1,10-phenanthrolines 5a−h. The results are shown in Scheme 2 and summarized in Table 1. The physical and spectral data are shown in Table 2.We examined the reaction of 2 with acetone, as a symmetrical ketone, in the presence of aqueous ammonia, which proceeded easily under mild conditions to afford selectively the desired 1,10-phenanthroline derivative 5a in 98% yield. It is noteworthy that the pyrido[3,2-h]quinazoline derivative, like 3, was not formed at all, in contrast to the reaction of 2 with aldehydes. 6 Similarly, 2-ethyl-3-methyl derivative 5b was also prepared quantitatively by the reaction of 2 with 3-pentanone under slightly forced conditions. Next, we attempted to carry out the reaction of 2 with cyclic ketones in order to synthesize 1,10-phenanthrolines fused by a cycloalkane ring. Expectedly, the desired ring-forming reaction of 2 with cyclopentanone, cyclohexanone and cycloheptanone took place cleanly at room temperature for 48 hours to afford 5c−e in almost quantitative yields. Further, the present reaction was applicable to some unsymmetrical ketones such as 2-butanone and 3-methyl-2-butanone. In both cases, the desired 1,10-phenanthrolines 5f, g were obta...

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A Facile and Convenient Synthetic Method for Fluorine-containing 1,2-Dihydropyrido[3,2-h]quinazolines and Pyrido[3,2-h]quinazolines

Cited by 10 publications

References 21 publications

Survey of Recent Literature Related to the Biologically Active 4(3H)-Quinazolinones Containing Fused Heterocycles

Survey of Recent Literature Related to the Biologically Active 4(3H)-Quinazolinones Containing Fused Heterocycles

A Green Synthesis of Pyrido[1,2‐a]quinazoline‐1,6‐dione Derivatives in Ionic Liquid Catalyzed by Iodine

A Simple and Efficient Synthetic Method for Fluorine-Containing 1,10-Phenanthrolines

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