Solid‐phase synthesis of a novel series of 2,3,4,5‐tetrahydro‐1,4‐benzodiazepin‐2,5‐dione libraries

Migihashi, Chiaki; Sato, Fuminori

doi:10.1002/jhet.5570400119

Cited by 11 publications

(9 citation statements)

References 22 publications

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“…The cyclative release feature of this approach resulted in a significant enhancement of the purity of the final compounds. In 2003, Mayer's method was applied by Migihashi to prepare a chemical library of 400 benzodiazepines employing an ACT-496 automatic synthesizer and IRORI radio-frequencyencoded split-mix synthesis technology [79]. Later, Fmoc-anthranilic acids were replaced with Boc-anthranilic acids, and a library of benzodiazepines was synthesized on a Wang resin [80] or on a Kaiser oxime resin [81].…”

Section: Benzo[b][14]diazepinesmentioning

confidence: 99%

Solid-Phase Synthesis of Seven-Membered Heterocycles with Two Nitrogen Atoms

Fülöpová

Soural

2017

Topics in Heterocyclic Chemistry

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Due to the importance of diazepines and diazepanes in medicinal chemistry and chemical biology, their preparation from diverse starting materials has been frequently reported. In this chapter, we summarize all strategies employing the method of solid-phase synthesis. More than seventeen different types of target compounds are accessible. The individual approaches are grouped according to the type of the target scaffold.

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Section: Benzo[b][14]diazepinesmentioning

confidence: 99%

Solid-Phase Synthesis of Seven-Membered Heterocycles with Two Nitrogen Atoms

Fülöpová

Soural

2017

Topics in Heterocyclic Chemistry

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“…Resin-bound anthranilic acids are important intermediates in the SP synthesis of six-membered fused 225−230 and seven-membered fused heterocyclic compounds. 197,231,232 A synthesis of quinazolin-4-(3H)-ones 225 with four points of diversity was developed using arylguanidines 723 (Scheme 133) as intermediates, and they readily underwent acid-mediated cyclative cleavage. Linear intermediates 723 were prepared from Fmoc-anthranilic acids (and also 3-amino-2-naphthoic acid), isothiocyanates, and secondary amines.…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…As a part of their study on 2-nitrobenzensulfonamides as advanced intermediates for the synthesis of diverse classes of The main sevenmembered rings of this type are 1,4-diazepane derivatives that are monocyclic, fused to alicycles, 239 benzannulated bicycles, 197,231,232,240 or tricyclic scaffolds. 241,242 Diazepane derivatives are considered privileged structures.…”

Section: Krchnǎḱ Et Al Reported Two Sp Syntheses Of Dihydroquinoxalin...mentioning

confidence: 99%

“…One year later, Migihashi and Sato developed a synthesis of 2,3,4,5-tetrahydro-1,4-benzodiazepin-2,5-diones derivatized at the benzene ring. 232 Linear precursors 782 (Scheme 144) were synthesized on Wang resin, which was acylated by Fmoc-amino acids, and then the Fmoc group was removed. Polymersupported amines 780 were reacted with 3-fluoro-6-nitrobenzoic acid.…”

Section: Krchnǎḱ Et Al Reported Two Sp Syntheses Of Dihydroquinoxalin...mentioning

confidence: 99%

“…Either Fmoc-anthranilic acid was coupled to the resin followed by Fmoc cleavage, or 2-nitrobenzoic acid − was immobilized, and the nitro group was reduced. Resin-bound anthranilic acids are important intermediates in the SP synthesis of six-membered fused − and seven-membered fused heterocyclic compounds. ,, …”

Section: Cyclative Cleavagementioning

confidence: 99%

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Traceless Solid-Phase Organic Synthesis

2019

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Traceless solid-phase synthesis represents an ultimate sophisticated synthetic strategy on insoluble supports. Compounds synthesized on solid supports can be released without a trace of the linker that was used to tether the intermediates during the synthesis. Thus, the target products are composed only of the components (atoms, functional groups) inherent to the target core structure. A wide variety of synthetic strategies have been developed to prepare products in a traceless manner, and this review is dedicated to all aspects of traceless solid-phase organic synthesis. Importantly, the synthesis does not need to be carried out on a linker designed for traceless synthesis; most of the synthetic approaches described herein were developed using standard, commercially available linkers (originally devised for solid-phase peptide synthesis). The type of structure prepared in a traceless fashion is not restricted. The individual synthetic approaches are divided into eight sections, each devoted to a different methodology for traceless synthesis. Each section consists of a brief outline of the synthetic strategy followed by a description of individual reported syntheses.

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