Special Issue "Molecules from Side Reactions"

A special issue of Molbank (ISSN 1422-8599). This special issue belongs to the section "Organic Synthesis".

Deadline for manuscript submissions: 31 October 2020.

Special Issue Editor

Dr. Stefano D’Errico
Website
Guest Editor
Department of Pharmacy, University of Naples Federico II, Via Domenico Montesano 49, 80131, Napoli, Italy
Interests: solid-phase synthesis; chemistry of nucleosides, nucleotides, and oligonucleotides; L-sugars; platinum complexes

Special Issue Information

Dear Colleagues,

Organic synthesis is a powerful tool that allows researchers to express their scientific creativity. Its fundamental role in obtaining drugs and creating new materials is irrefutable evidence. However, a chemical process may often take a side route, generating novel unexplored products. The purpose of this Special Issue is to collect papers reporting on the synthesis and characterization of these compounds that could be useful building blocks for the whole scientific community.

Dr. Stefano D’Errico
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molbank is an international peer-reviewed open access quarterly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 350 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Organic synthesis
  • Solid-phase synthesis
  • Heterocycles
  • Building blocks
  • Intermediates
  • Medicinal chemistry
  • Chemical diversity
  • Carbon–carbon bond formation
  • Metal-mediated reactions
  • Drug design

Published Papers (12 papers)

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Research

Open AccessShort Note
4′-(N-(Propan-1,2-dienyl)pyrrol-2-yl)-2,2′:6′,2″-terpyridine
Molbank 2020, 2020(2), M1142; https://doi.org/10.3390/M1142 - 10 Jun 2020
Abstract
A new pyrrole-substituted terpyridine derivative that possesses an allene moiety was obtained as an “unexpected” sole product during an attempt to alkylate the N-atom of pyrrole with propargyl bromide in order to obtain an alkyne-functionalized terpyridine. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessFeature PaperCommunication
Formation of an Isomeric Mixture of Dienynes Instead of a Diallene
Molbank 2020, 2020(2), M1133; https://doi.org/10.3390/M1133 - 11 May 2020
Abstract
Attempts to convert 1,1,2,2,7,7,8,8-octaethoxyocta-3,5-diyne to a symmetric allene by reduction with lithium aluminum hydride failed. Instead reduction accompanied by isomerization occurred and afforded 1,1,2,7,8,8-hexaethoxyocta-2,6-dien-4-yne as a mixture of three isomers in 63% total isolated yield. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessCommunication
Unexpected Seven-Membered Ring Formation for Muraymycin-Type Nucleoside-Peptide Antibiotics
Molbank 2020, 2020(2), M1122; https://doi.org/10.3390/M1122 - 26 Mar 2020
Abstract
Naturally occurring nucleoside-peptide antibiotics such as muraymycins or caprazamycins are of major interest for the development of novel antibacterial agents. However, the synthesis of new analogues of these natural products for structure–activity relationship (SAR) studies is challenging. In our synthetic efforts towards a [...] Read more.
Naturally occurring nucleoside-peptide antibiotics such as muraymycins or caprazamycins are of major interest for the development of novel antibacterial agents. However, the synthesis of new analogues of these natural products for structure–activity relationship (SAR) studies is challenging. In our synthetic efforts towards a muraymycin-derived nucleoside building block suitable for attachment to a solid support, we came across an interesting side product. This compound resulted from an undesired Fmoc deprotection with subsequent cyclization, thus furnishing a remarkable caprazamycin-like seven-membered diazepanone ring. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessCommunication
8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity
Molbank 2020, 2020(1), M1119; https://doi.org/10.3390/M1119 - 06 Mar 2020
Abstract
3′,5′-O-Bis(tert-butyldimethylsilyl)-8-fluoro-N-2-isobutyryl-2′-deoxyguanosine was synthesized from 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-isobutyryl-2′-deoxyguanosine by the treatment with N-fluorobenzenesulfonimide. A similar fluorination reaction with 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-(N,N-dimethylformamidine)-2′-deoxyguanosine, however, failed to give [...] Read more.
3′,5′-O-Bis(tert-butyldimethylsilyl)-8-fluoro-N-2-isobutyryl-2′-deoxyguanosine was synthesized from 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-isobutyryl-2′-deoxyguanosine by the treatment with N-fluorobenzenesulfonimide. A similar fluorination reaction with 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-(N,N-dimethylformamidine)-2′-deoxyguanosine, however, failed to give the corresponding fluorinated product. It was found that 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine is labile under acidic conditions, but sufficiently stable in dichloroacetic acid used in solid phase synthesis. Incorporation of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis failed to give the desired products. Furthermore, treatment of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine with aqueous ammonium hydroxide did not give 8-fluoro-2′-deoxyguanosine, but led to the formation of a mixture consisting of 8-amino-N-2-isobutyryl-2′-deoxyguanosine and C8:5′-O-cyclo-2′-deoxyguanosine. Taken together, an alternative N-protecting group and possibly modified solid phase synthetic cycle conditions will be required for the incorporation of 8-fluoro-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
Open AccessCommunication
Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block
Molbank 2020, 2020(1), M1111; https://doi.org/10.3390/M1111 - 18 Jan 2020
Abstract
Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to [...] Read more.
Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to the diastereomeric sulfoxide products was achieved. The product was fully characterized by 1H, 13C and 2D NMR alongside MS analysis. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessCommunication
Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses
Molbank 2020, 2020(1), M1108; https://doi.org/10.3390/M1108 - 14 Jan 2020
Abstract
During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation [...] Read more.
During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation of the pure epoxide was not possible since a rapid reversible conversion accompanied by the migration of the ester group took place and resulted in the formation of an unusual oxetane-bridged disaccharide scaffold. X-ray diffractometric structure elucidation and the suggested mechanism of the rearrangement are provided. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessShort Note
N′-Acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide
Molbank 2020, 2020(1), M1104; https://doi.org/10.3390/M1104 - 07 Jan 2020
Abstract
Synthesis of N′-acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide from the phenyl acetates of 3-acetyl-5-(3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl in alkaline medium and its characterization by spectroscopic methods. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
Open AccessShort Note
N-(2-Hydroxy-1,1-dimethylethyl)-3-methylbenzamide
Molbank 2020, 2020(1), M1099; https://doi.org/10.3390/M1099 - 19 Dec 2019
Cited by 2
Abstract
The title compound, N-(2-hydroxy-1,1-dimethylethyl)-3-methylbenzamide was synthesized by reacting 3-methylbenzoyl chloride or 3-methylbenzoic acid with 2-amino-2-methyl-1-propanol. In the present report, the synthesized target compound was fully characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS), its composition confirmed [...] Read more.
The title compound, N-(2-hydroxy-1,1-dimethylethyl)-3-methylbenzamide was synthesized by reacting 3-methylbenzoyl chloride or 3-methylbenzoic acid with 2-amino-2-methyl-1-propanol. In the present report, the synthesized target compound was fully characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS), its composition confirmed by elemental analysis, and its structure determined and confirmed by X-ray analysis. The importance of this compound lies in its possession of an N,O-bidentate directing group. Such a structural motif is potentially suitable for metal-catalyzed C–H bond functionalization reactions. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
Open AccessFeature PaperShort Note
5′-Chloro-5′-deoxy-2′,3′-O-isopropylidene-6-fluoro nebularine
Molbank 2019, 2019(4), M1097; https://doi.org/10.3390/M1097 - 13 Dec 2019
Abstract
In this paper, we report on the synthesis and spectroscopic characterization of the novel nucleoside 5′-chloro-5′-deoxy-2′,3′-O-isopropylidene-6-fluoro nebularine, obtained as a side product during the second step of the synthesis of 5′-fluoro-5′-deoxy-5-aminoimidazole-4-carboxamide-β-d-riboside (5′-F-AICAR), a non-phosphorylable analogue of 5-aminoimidazole-4-carboxamide-β-d-riboside (AICAR). Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessCommunication
Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone
Molbank 2019, 2019(4), M1096; https://doi.org/10.3390/M1096 - 10 Dec 2019
Abstract
2,3,5-Tri-O-benzyl- and 2,3,5-tri-O-methyl-d-ribono-γ-lactone were converted with (methoxyethoxymethoxy)methyl and benzyloxy tributylstannane into the corresponding protected d-psicoses as mixtures of anomers in 31%–72% yield. Treatment of 2,3,5-tri-O-methyl-l-ribono-γ-lactone with benzyloxy tributylstannane afforded the corresponding l [...] Read more.
2,3,5-Tri-O-benzyl- and 2,3,5-tri-O-methyl-d-ribono-γ-lactone were converted with (methoxyethoxymethoxy)methyl and benzyloxy tributylstannane into the corresponding protected d-psicoses as mixtures of anomers in 31%–72% yield. Treatment of 2,3,5-tri-O-methyl-l-ribono-γ-lactone with benzyloxy tributylstannane afforded the corresponding l-psicose derivative as an anomeric mixture in 72% yield. Both methylated psicoses were further converted into 1,2-O-isopropylidene-3,4,6-tri-O-methyl-d- and l-psicofuranosides, the respective α- and β-anomers of which could be separated and characterized. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Open AccessCommunication
Pyridine-Imidazlolium Salts: Oxidatively Cleavage of N-C Bond via Nitration
Molbank 2019, 2019(4), M1095; https://doi.org/10.3390/M1095 - 23 Nov 2019
Abstract
Azaheterocycles derivatives with pyridine-imidazole skeleton are compounds of great value for medicinal chemistry. We report herein the nitration of 1,1′-(pyridine-2,6-diylbis(methylene))bis{3-[2-(4-nitrophenyl)-2-oxoethyl]-1H-imidazol-3-ium} bromide using a typical mixture of nitric and sulphuric acid. The nitration occur with the oxidative cleavage of N–C bond between [...] Read more.
Azaheterocycles derivatives with pyridine-imidazole skeleton are compounds of great value for medicinal chemistry. We report herein the nitration of 1,1′-(pyridine-2,6-diylbis(methylene))bis{3-[2-(4-nitrophenyl)-2-oxoethyl]-1H-imidazol-3-ium} bromide using a typical mixture of nitric and sulphuric acid. The nitration occur with the oxidative cleavage of N–C bond between imidazolium ring and methylene group. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
Open AccessShort Note
(E)-4-(3-Phenylisoxazol-5-yl)but-3-en-2-one
Molbank 2019, 2019(3), M1081; https://doi.org/10.3390/M1081 - 18 Sep 2019
Abstract
(E)-4-(3-Phenylisoxazol-5-yl)but-3-en-2-one was synthesized via the oxidative ring opening reaction of 2-(5-methylfuran-2-yl)-1-phenylethanone oxime, followed by the iodine mediated isomerization. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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