Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles

The purpose of this reprint is to introduce the reader to the latest advances in the chemistry of N-heterocycles, such as the synthesis, reactivity, and applications of aromatic and saturated nitrogen heterocyclic compounds. The role of N-heterocycles in human life is difficult to overestimate; thei...

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description The purpose of this reprint is to introduce the reader to the latest advances in the chemistry of N-heterocycles, such as the synthesis, reactivity, and applications of aromatic and saturated nitrogen heterocyclic compounds. The role of N-heterocycles in human life is difficult to overestimate; their diverse application spans from the pharmaceutical industry to the production of energetic materials, dyes, and non-linear optical materials, among many other areas. With this reprint, we aim to highlight the most recent and most promising research results in this field, presented in the form of original articles and high-quality reviews.
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institution Directory of Open Access Books
language eng
publishDate 2025
publishDateRange 2025
publishDateSort 2025
publisher MDPI - Multidisciplinary Digital Publishing Institute
publisherStr MDPI - Multidisciplinary Digital Publishing Institute
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spelling doab-20.500.12854ir-1527392025-02-20T12:59:40Z Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles Starosotnikov, Alexey M. Bastrakov, Maxim A. Dalinger, Igor L. C–H functionalization cyclization indazole products transition metals catalysis nitro compounds Azolo[1,5-a]pyrimidines CK2 inhibition antitumor activity multicomponent reaction amides BF3·Et2O debenzylation nitrogen heterocycles 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate anthranilamide ethyl levulinate Amberlyst® 15 Brønsted acid cascade reaction mechanochemistry quinazolinone ball mill azirines pyrrolines cycloaddition annulation copper catalysis nitro group nitropyridines bis-(het)aryl ethenes nucleophilic substitution thiols UV–Vis spectroscopy alkoxides aziridination manganese iminoiodinane energetic materials tetrazine hydroxytetrazole oxadiazole sulfonylureas DPP-IV inhibitors diabetes mellitus peptidomimetics alkynes enediynes heterocycles benzo[b]thiophene Bergman cyclization Nicholas reaction Sonogashira coupling benzenesulfonamides antifolates folic acids synthesis applications drugs aziridine non-activated nucleophilic ring-opening regioselectivity pyrrole domino reaction 1H-indole synthesis aza–Michael reaction SNAr reaction heteroaromatization 4-hydroxy-2-pyrone 4-pyridone aminoenone trifluoromethylated heterocycles regioselective reactions oxidative cyclization manganese(IV) oxide 1,2,4-triazine phenols cross-coupling spiropyrrolidine derivatives antimicrobial antioxidant antidiabetic ADME molecular docking and dynamic simulation sulfur–nitrogen heterocycles benzo[1,2-d:4,5-d’]bis([1,2,3]thiadiazole) aromatic nucleophilic substitution Suzuki and Stille cross-coupling reactions X-ray analysis estradiol benzisoxazole hybrid cancer selectivity apoptosis induction carborane tetrazole HEMDs DFT single crystal X-ray diffraction electrochemistry imidazoles vinyl azides click chemistry mechanochemical synthesis 1,2,3-triazole cycloaddition reaction Rufinamide synthesis solvent-free C-glycosyl compound amidrazone IEDDA pyridine aminofurazans fused furazans perchlorates energetic compound impact sensitivity thermal decomposition combustion burning rate 1,2,3-triazoles nucleobases Lewis acid molecular docking donor–acceptor cyclopropanes primary amines pyrrolidin-2-ones benz[g]indolizidines acetylenes amino acids C-H activation catalysis isoquinolones active methylene thioamides Michael addition dithiomalondianilide cyanoacetic esters [1,2]dithiolo[3,4-b]pyridines herbicide safeners azomethine ylide pyrrolidine spiro-compound imidazole medicinal chemistry drug discovery Minisci reaction heterogeneous photocatalysis N-hydroxyphthalimide titanium dioxide green chemistry visible light photocatalysis 2-hydroxyphenyl group hydrogen bond ESIPT luminescence [1,2,4]triazolo[4,3-c]quinazolines fluorescence solvatochromism pH-sensor multicomponent domino cyclizations ethyl trifluoropyruvate methyl ketones amino alcohols γ-lactams tetrahydropyrrolo[2,1-b]oxazolones tetrahydropyrrolo[2,1-b]oxazinones alkaloid Maillard reaction crystallization-induced diastereomer transformation glutamine hydroxy amino acid diketopiperazine thiourea dioxide TDO pyridazine pyrimidine pyrazine organophosphorus compounds dipyrroloquinoxaline bathochromic shift substituent effect energy gap N-trifluoromethyl group imidates iminonitriles nitrostyrenes 2-aminopyridine N-heterocycles 1,3,4-oxadiazole D-ribose L-amino acid pyrrole-2-carbaldehyde iodine effect antibacterial activity sustainable synthesis aromatic N-heterocycles solid acids nanoparticles microwaves ultrasounds visible light activation high hydrostatic pressure biomass 1,3-diynamides ynamides homogeneous catalysis annulation reactions cycloaddition cascade reactions helical twisted frontier molecular orbitals (Hel-FMO) Hexa-dehydro-Diels–Alder (HDDA) reaction quinolines indoles carbazoles N-heterocyclic-based dyes photosensitizers photodynamic therapy thema EDItEUR::G Reference, Information and Interdisciplinary subjects::GP Research and information: general thema EDItEUR::P Mathematics and Science::PH Physics::PHH Thermodynamics and heat The purpose of this reprint is to introduce the reader to the latest advances in the chemistry of N-heterocycles, such as the synthesis, reactivity, and applications of aromatic and saturated nitrogen heterocyclic compounds. The role of N-heterocycles in human life is difficult to overestimate; their diverse application spans from the pharmaceutical industry to the production of energetic materials, dyes, and non-linear optical materials, among many other areas. With this reprint, we aim to highlight the most recent and most promising research results in this field, presented in the form of original articles and high-quality reviews. 2025-02-20T12:59:38Z 2025-02-20T12:59:38Z 2024 book ONIX_20250220_9783725820818_103 9783725820818 9783725820825 https://directory.doabooks.org/handle/20.500.12854/152739 eng application/octet-stream Attribution 4.0 International https://mdpi.com/books/pdfview/book/9882 MDPI - Multidisciplinary Digital Publishing Institute 10.3390/books978-3-7258-2082-5 10.3390/books978-3-7258-2082-5 46cabcaa-dd94-4bfe-87b4-55023c1b36d0 9783725820818 9783725820825 544 Basel open access
spellingShingle C–H functionalization
cyclization
indazole products
transition metals catalysis
nitro compounds
Azolo[1,5-a]pyrimidines
CK2 inhibition
antitumor activity
multicomponent reaction
amides
BF3·Et2O
debenzylation
nitrogen heterocycles
2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate
anthranilamide
ethyl levulinate
Amberlyst® 15
Brønsted acid
cascade reaction
mechanochemistry
quinazolinone
ball mill
azirines
pyrrolines
cycloaddition
annulation
copper catalysis
nitro group
nitropyridines
bis-(het)aryl ethenes
nucleophilic substitution
thiols
UV–Vis spectroscopy
alkoxides
aziridination
manganese
iminoiodinane
energetic materials
tetrazine
hydroxytetrazole
oxadiazole
sulfonylureas
DPP-IV inhibitors
diabetes mellitus
peptidomimetics
alkynes
enediynes
heterocycles
benzo[b]thiophene
Bergman cyclization
Nicholas reaction
Sonogashira coupling
benzenesulfonamides
antifolates
folic acids
synthesis
applications
drugs
aziridine
non-activated
nucleophilic
ring-opening
regioselectivity
pyrrole
domino reaction
1H-indole synthesis
aza–Michael reaction
SNAr reaction
heteroaromatization
4-hydroxy-2-pyrone
4-pyridone
aminoenone
trifluoromethylated heterocycles
regioselective reactions
oxidative cyclization
manganese(IV) oxide
1,2,4-triazine
phenols
cross-coupling
spiropyrrolidine derivatives
antimicrobial
antioxidant
antidiabetic
ADME
molecular docking and dynamic simulation
sulfur–nitrogen heterocycles
benzo[1,2-d:4,5-d’]bis([1,2,3]thiadiazole)
aromatic nucleophilic substitution
Suzuki and Stille cross-coupling reactions
X-ray analysis
estradiol
benzisoxazole
hybrid
cancer selectivity
apoptosis induction
carborane
tetrazole
HEMDs
DFT
single crystal X-ray diffraction
electrochemistry
imidazoles
vinyl azides
click chemistry
mechanochemical synthesis
1,2,3-triazole
cycloaddition reaction
Rufinamide synthesis
solvent-free
C-glycosyl compound
amidrazone
IEDDA
pyridine
aminofurazans
fused furazans
perchlorates
energetic compound
impact sensitivity
thermal decomposition
combustion
burning rate
1,2,3-triazoles
nucleobases
Lewis acid
molecular docking
donor–acceptor cyclopropanes
primary amines
pyrrolidin-2-ones
benz[g]indolizidines
acetylenes
amino acids
C-H activation
catalysis
isoquinolones
active methylene thioamides
Michael addition
dithiomalondianilide
cyanoacetic esters
[1,2]dithiolo[3,4-b]pyridines
herbicide safeners
azomethine ylide
pyrrolidine
spiro-compound
imidazole
medicinal chemistry
drug discovery
Minisci reaction
heterogeneous photocatalysis
N-hydroxyphthalimide
titanium dioxide
green chemistry
visible light photocatalysis
2-hydroxyphenyl group
hydrogen bond
ESIPT
luminescence
[1,2,4]triazolo[4,3-c]quinazolines
fluorescence
solvatochromism
pH-sensor
multicomponent domino cyclizations
ethyl trifluoropyruvate
methyl ketones
amino alcohols
γ-lactams
tetrahydropyrrolo[2,1-b]oxazolones
tetrahydropyrrolo[2,1-b]oxazinones
alkaloid
Maillard reaction
crystallization-induced diastereomer transformation
glutamine
hydroxy amino acid
diketopiperazine
thiourea dioxide
TDO
pyridazine
pyrimidine
pyrazine
organophosphorus compounds
dipyrroloquinoxaline
bathochromic shift
substituent effect
energy gap
N-trifluoromethyl group
imidates
iminonitriles
nitrostyrenes
2-aminopyridine
N-heterocycles
1,3,4-oxadiazole
D-ribose
L-amino acid
pyrrole-2-carbaldehyde
iodine effect
antibacterial activity
sustainable synthesis
aromatic N-heterocycles
solid acids
nanoparticles
microwaves
ultrasounds
visible light activation
high hydrostatic pressure
biomass
1,3-diynamides
ynamides
homogeneous catalysis
annulation reactions
cycloaddition cascade reactions
helical twisted frontier molecular orbitals (Hel-FMO)
Hexa-dehydro-Diels–Alder (HDDA) reaction
quinolines
indoles
carbazoles
N-heterocyclic-based dyes
photosensitizers
photodynamic therapy
thema EDItEUR::G Reference, Information and Interdisciplinary subjects::GP Research and information: general
thema EDItEUR::P Mathematics and Science::PH Physics::PHH Thermodynamics and heat
Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles
title Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles
title_full Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles
title_fullStr Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles
title_full_unstemmed Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles
title_short Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles
title_sort recent developments in the synthesis and functionalization of nitrogen heterocycles
topic C–H functionalization
cyclization
indazole products
transition metals catalysis
nitro compounds
Azolo[1,5-a]pyrimidines
CK2 inhibition
antitumor activity
multicomponent reaction
amides
BF3·Et2O
debenzylation
nitrogen heterocycles
2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate
anthranilamide
ethyl levulinate
Amberlyst® 15
Brønsted acid
cascade reaction
mechanochemistry
quinazolinone
ball mill
azirines
pyrrolines
cycloaddition
annulation
copper catalysis
nitro group
nitropyridines
bis-(het)aryl ethenes
nucleophilic substitution
thiols
UV–Vis spectroscopy
alkoxides
aziridination
manganese
iminoiodinane
energetic materials
tetrazine
hydroxytetrazole
oxadiazole
sulfonylureas
DPP-IV inhibitors
diabetes mellitus
peptidomimetics
alkynes
enediynes
heterocycles
benzo[b]thiophene
Bergman cyclization
Nicholas reaction
Sonogashira coupling
benzenesulfonamides
antifolates
folic acids
synthesis
applications
drugs
aziridine
non-activated
nucleophilic
ring-opening
regioselectivity
pyrrole
domino reaction
1H-indole synthesis
aza–Michael reaction
SNAr reaction
heteroaromatization
4-hydroxy-2-pyrone
4-pyridone
aminoenone
trifluoromethylated heterocycles
regioselective reactions
oxidative cyclization
manganese(IV) oxide
1,2,4-triazine
phenols
cross-coupling
spiropyrrolidine derivatives
antimicrobial
antioxidant
antidiabetic
ADME
molecular docking and dynamic simulation
sulfur–nitrogen heterocycles
benzo[1,2-d:4,5-d’]bis([1,2,3]thiadiazole)
aromatic nucleophilic substitution
Suzuki and Stille cross-coupling reactions
X-ray analysis
estradiol
benzisoxazole
hybrid
cancer selectivity
apoptosis induction
carborane
tetrazole
HEMDs
DFT
single crystal X-ray diffraction
electrochemistry
imidazoles
vinyl azides
click chemistry
mechanochemical synthesis
1,2,3-triazole
cycloaddition reaction
Rufinamide synthesis
solvent-free
C-glycosyl compound
amidrazone
IEDDA
pyridine
aminofurazans
fused furazans
perchlorates
energetic compound
impact sensitivity
thermal decomposition
combustion
burning rate
1,2,3-triazoles
nucleobases
Lewis acid
molecular docking
donor–acceptor cyclopropanes
primary amines
pyrrolidin-2-ones
benz[g]indolizidines
acetylenes
amino acids
C-H activation
catalysis
isoquinolones
active methylene thioamides
Michael addition
dithiomalondianilide
cyanoacetic esters
[1,2]dithiolo[3,4-b]pyridines
herbicide safeners
azomethine ylide
pyrrolidine
spiro-compound
imidazole
medicinal chemistry
drug discovery
Minisci reaction
heterogeneous photocatalysis
N-hydroxyphthalimide
titanium dioxide
green chemistry
visible light photocatalysis
2-hydroxyphenyl group
hydrogen bond
ESIPT
luminescence
[1,2,4]triazolo[4,3-c]quinazolines
fluorescence
solvatochromism
pH-sensor
multicomponent domino cyclizations
ethyl trifluoropyruvate
methyl ketones
amino alcohols
γ-lactams
tetrahydropyrrolo[2,1-b]oxazolones
tetrahydropyrrolo[2,1-b]oxazinones
alkaloid
Maillard reaction
crystallization-induced diastereomer transformation
glutamine
hydroxy amino acid
diketopiperazine
thiourea dioxide
TDO
pyridazine
pyrimidine
pyrazine
organophosphorus compounds
dipyrroloquinoxaline
bathochromic shift
substituent effect
energy gap
N-trifluoromethyl group
imidates
iminonitriles
nitrostyrenes
2-aminopyridine
N-heterocycles
1,3,4-oxadiazole
D-ribose
L-amino acid
pyrrole-2-carbaldehyde
iodine effect
antibacterial activity
sustainable synthesis
aromatic N-heterocycles
solid acids
nanoparticles
microwaves
ultrasounds
visible light activation
high hydrostatic pressure
biomass
1,3-diynamides
ynamides
homogeneous catalysis
annulation reactions
cycloaddition cascade reactions
helical twisted frontier molecular orbitals (Hel-FMO)
Hexa-dehydro-Diels–Alder (HDDA) reaction
quinolines
indoles
carbazoles
N-heterocyclic-based dyes
photosensitizers
photodynamic therapy
thema EDItEUR::G Reference, Information and Interdisciplinary subjects::GP Research and information: general
thema EDItEUR::P Mathematics and Science::PH Physics::PHH Thermodynamics and heat
topic_facet C–H functionalization
cyclization
indazole products
transition metals catalysis
nitro compounds
Azolo[1,5-a]pyrimidines
CK2 inhibition
antitumor activity
multicomponent reaction
amides
BF3·Et2O
debenzylation
nitrogen heterocycles
2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate
anthranilamide
ethyl levulinate
Amberlyst® 15
Brønsted acid
cascade reaction
mechanochemistry
quinazolinone
ball mill
azirines
pyrrolines
cycloaddition
annulation
copper catalysis
nitro group
nitropyridines
bis-(het)aryl ethenes
nucleophilic substitution
thiols
UV–Vis spectroscopy
alkoxides
aziridination
manganese
iminoiodinane
energetic materials
tetrazine
hydroxytetrazole
oxadiazole
sulfonylureas
DPP-IV inhibitors
diabetes mellitus
peptidomimetics
alkynes
enediynes
heterocycles
benzo[b]thiophene
Bergman cyclization
Nicholas reaction
Sonogashira coupling
benzenesulfonamides
antifolates
folic acids
synthesis
applications
drugs
aziridine
non-activated
nucleophilic
ring-opening
regioselectivity
pyrrole
domino reaction
1H-indole synthesis
aza–Michael reaction
SNAr reaction
heteroaromatization
4-hydroxy-2-pyrone
4-pyridone
aminoenone
trifluoromethylated heterocycles
regioselective reactions
oxidative cyclization
manganese(IV) oxide
1,2,4-triazine
phenols
cross-coupling
spiropyrrolidine derivatives
antimicrobial
antioxidant
antidiabetic
ADME
molecular docking and dynamic simulation
sulfur–nitrogen heterocycles
benzo[1,2-d:4,5-d’]bis([1,2,3]thiadiazole)
aromatic nucleophilic substitution
Suzuki and Stille cross-coupling reactions
X-ray analysis
estradiol
benzisoxazole
hybrid
cancer selectivity
apoptosis induction
carborane
tetrazole
HEMDs
DFT
single crystal X-ray diffraction
electrochemistry
imidazoles
vinyl azides
click chemistry
mechanochemical synthesis
1,2,3-triazole
cycloaddition reaction
Rufinamide synthesis
solvent-free
C-glycosyl compound
amidrazone
IEDDA
pyridine
aminofurazans
fused furazans
perchlorates
energetic compound
impact sensitivity
thermal decomposition
combustion
burning rate
1,2,3-triazoles
nucleobases
Lewis acid
molecular docking
donor–acceptor cyclopropanes
primary amines
pyrrolidin-2-ones
benz[g]indolizidines
acetylenes
amino acids
C-H activation
catalysis
isoquinolones
active methylene thioamides
Michael addition
dithiomalondianilide
cyanoacetic esters
[1,2]dithiolo[3,4-b]pyridines
herbicide safeners
azomethine ylide
pyrrolidine
spiro-compound
imidazole
medicinal chemistry
drug discovery
Minisci reaction
heterogeneous photocatalysis
N-hydroxyphthalimide
titanium dioxide
green chemistry
visible light photocatalysis
2-hydroxyphenyl group
hydrogen bond
ESIPT
luminescence
[1,2,4]triazolo[4,3-c]quinazolines
fluorescence
solvatochromism
pH-sensor
multicomponent domino cyclizations
ethyl trifluoropyruvate
methyl ketones
amino alcohols
γ-lactams
tetrahydropyrrolo[2,1-b]oxazolones
tetrahydropyrrolo[2,1-b]oxazinones
alkaloid
Maillard reaction
crystallization-induced diastereomer transformation
glutamine
hydroxy amino acid
diketopiperazine
thiourea dioxide
TDO
pyridazine
pyrimidine
pyrazine
organophosphorus compounds
dipyrroloquinoxaline
bathochromic shift
substituent effect
energy gap
N-trifluoromethyl group
imidates
iminonitriles
nitrostyrenes
2-aminopyridine
N-heterocycles
1,3,4-oxadiazole
D-ribose
L-amino acid
pyrrole-2-carbaldehyde
iodine effect
antibacterial activity
sustainable synthesis
aromatic N-heterocycles
solid acids
nanoparticles
microwaves
ultrasounds
visible light activation
high hydrostatic pressure
biomass
1,3-diynamides
ynamides
homogeneous catalysis
annulation reactions
cycloaddition cascade reactions
helical twisted frontier molecular orbitals (Hel-FMO)
Hexa-dehydro-Diels–Alder (HDDA) reaction
quinolines
indoles
carbazoles
N-heterocyclic-based dyes
photosensitizers
photodynamic therapy
thema EDItEUR::G Reference, Information and Interdisciplinary subjects::GP Research and information: general
thema EDItEUR::P Mathematics and Science::PH Physics::PHH Thermodynamics and heat
url ONIX_20250220_9783725820818_103