One-Pot Synthesis of 2,5-Disubstituted Pyrimidines from Nitriles

Frutos, Rogelio P.; Wei, Xudong; Patel, Nitinchandra D.; Tampone, Thomas G.; Mulder, Jason A.; Busacca, Carl A.; Senanayake, Chris H.

doi:10.1021/jo400720p

Cited by 26 publications

(13 citation statements)

References 22 publications

(16 reference statements)

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“…Cyclization of 15a – c was achieved by boiling in glacial acetic acid to yield the azabenzimidazole intermediates 16a – c , which were then converted into the diamidines 17a – c by the Pinner process. 32,33,39 …”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Heterocyclic Cations for Specific DNA Recognition: From AT-Rich to Mixed-Base-Pair DNA Sequences

et al. 2014

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The compounds synthesized in this research were designed with the goal of establishing a new paradigm for mixed-base-pair DNA sequence-specific recognition. The design scheme starts with a cell-permeable heterocyclic cation that binds to AT base pair sites in the DNA minor groove. Modifications were introduced in the original compound to include an H-bond accepting group to specifically recognize the G-NH that projects into the minor groove. Therefore, a series of heterocyclic cations substituted with an azabenzimidazole ring has been designed and synthesized for mixed-base-pair DNA recognition. The most successful compound, 12a, had an azabenzimidazole to recognize G and additional modifications for general minor groove interactions. It binds to the DNA site −AAAGTTT– more strongly than the −AAATTT– site without GC and indicates the design success. Structural modifications of 12a generally weakened binding. The interactions of the new compound with a variety of DNA sequences with and without GC base pairs were evaluated by thermal melting analysis, circular dichroism, fluorescence emission spectroscopy, surface plasmon resonance, and molecular modeling.

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Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Heterocyclic Cations for Specific DNA Recognition: From AT-Rich to Mixed-Base-Pair DNA Sequences

et al. 2014

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“…An original one‐pot synthesis from nitriles was reported by Frutos and Wei . The nitrile is converted into the corresponding amidine by a classical strategy, and this is directly condensed with 3‐chloro‐ or 3‐phenylvinamidinium salts 10 to yield the corresponding 2,5‐disubstituted pyrimidines in good yields (Scheme ).…”

Section: Pinner‐type Synthesismentioning

confidence: 99%

Recent Approaches to the Synthesis of Pyrimidine Derivatives

et al. 2017

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“…This practically controlled approach involves the formation of amidine 342 intermediates by reaction of ammonia and imidates 341 (a hydrochloride salt of imidate ester formed in the presence of HCl and methanol from nitriles 340) and finally a competitive reaction of vinamidinium salt 343 with amidines 342 gives pyrimidines (Scheme 98). The selectivity of vinamidinium salt for the amidate formation is crucial for the selective synthesis of substituted pyrimidines 344 [209]. Another important methodology reported for pyrimidine synthesis involves the three-component reaction of aldehydes 345 with malononitrile 45 and thiourea/urea 346 in the presence of phosphorus pentoxide [210].…”

Section: Synthesis Of Pyrimidinesmentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

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One-Pot Synthesis of 2,5-Disubstituted Pyrimidines from Nitriles

Abstract: A practical, one-step process for the synthesis of 2,5-disubstituted pyrimidines is presented. The protocol proved to be general for the synthesis of a variety of pyrimidine-containing compounds bearing an assortment of functional groups.

Cited by 26 publications

References 22 publications

Design and Synthesis of Heterocyclic Cations for Specific DNA Recognition: From AT-Rich to Mixed-Base-Pair DNA Sequences

Design and Synthesis of Heterocyclic Cations for Specific DNA Recognition: From AT-Rich to Mixed-Base-Pair DNA Sequences

Recent Approaches to the Synthesis of Pyrimidine Derivatives

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

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