Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Four Extra Heteroatoms 2:2

Claraz, Aurélie

doi:10.1016/b978-0-12-818655-8.00086-x

Cited by 2 publications

(5 citation statements)

References 188 publications

(210 reference statements)

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“…For a structural description in combination with the HPs' nomenclature, the general formula (1) can be applied for recognising the appropriate hetarene [11] according to: hetaryl[m,n-p]hetarene (1) where m,n are numbers of carbon atoms shared by both rings, the p-junction mode reveals the shared bond, hetaryl is the name of a five-membered heterocycle in a prefix, and hetarene is the name of a superior five-membered heterocycle [1,4,6,7,11]. Structure of general types of HPs containing two heteroatoms, one per core, according to Ramsden's classification [4,11]: I-hetaryl [3,2-b]hetarene (1,4-diheteropentalene), II-hetaryl [2,3c]hetarene = hetaryl [3,4-b]hetarene (1,5-diheteropentalene), III-hetaryl [2,3-b]hetarene (1,6-diheteropentalene), IV-hetaryl [3,4-c]hetarene (2,5-diheteropentalene).…”

Section: Figurementioning

confidence: 99%

“…where m,n are numbers of carbon atoms shared by both rings, the p-junction mode reveals the shared bond, hetaryl is the name of a five-membered heterocycle in a prefix, and hetarene is the name of a superior five-membered heterocycle [1,4,6,7,11].…”

Section: Figurementioning

confidence: 99%

“…Since the first Ramsden's classification of HPs into four general types (I-IV, Figure 2) in 1977 [4,5], the number of identified 5-5 bicyclic regioisomers with two heteroatoms, one for each core (1:1), has increased dramatically [1,6]. The presence of four heteroatoms in a structure, two per core (2:2), has led to the rise of basic structural prototypes up to sixteen [7]. Undoubtedly, through the addition of more heteroatoms into the bicyclic system and by variations in modes of fusion altogether, including the non-classical heteropentalenes and betaines, the number of possible isoconjugates has reached an uncountable number.…”

Section: Introductionmentioning

confidence: 99%

“…Undoubtedly, through the addition of more heteroatoms into the bicyclic system and by variations in modes of fusion altogether, including the non-classical heteropentalenes and betaines, the number of possible isoconjugates has reached an uncountable number. Generally, oxygen, sulphur, nitrogen, selenium and tellurium are the most commonly employed as heteroatoms [1][2][3][4][5][6][7],…”

Section: Introductionmentioning

confidence: 99%

“…Reactions 2023, 4, FOR PEER REVIEW altogether, including the non-classical heteropentalenes and betaines, the number of pos sible isoconjugates has reached an uncountable number. Generally, oxygen, sulphur, ni trogen, selenium and tellurium are the most commonly employed as heteroatoms [1][2][3][4][5][6][7] but a few reports on HPs with phosphorus [8], boron [9] or silicon [10] in the position o heteroatom have recently been published. For a structural description in combination with the HPs' nomenclature, the genera formula (1) can be applied for recognising the appropriate hetarene [11] according to:…”

Section: Introductionmentioning

confidence: 99%

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Hemetsberger–Knittel and Ketcham Synthesis of Heteropentalenes with Two (1:1), Three (1:2)/(2:1) and Four (2:2) Heteroatoms

et al. 2023

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The synthetic methods leading to furo[3,2-b]pyrroles and thiazolo [5,4-d]thiazoles are reviewed herein. Furo-, thieno- and seleno [3,2-b]pyrroles are related to heteropentalenes, containing two heteroatoms in the entire structure, one each per core. The synthetic approach follows the Hemetsberger–Knittel protocol covering three reaction steps—the nucleophilic substitution of halogen-containing aliphatic carboxylic acid esters, Knoevenagel condensation and, finally, thermolysis promoting the intramolecular cyclocondensation to O,N-heteropentalene. The Hemetsberger–Knittel reaction sequence is also known for the preparation of O,N-heteropentalenes with three heteroatoms (2:1) and their sulphur and selen heteroatoms containing structural analogues and bispyrroles. The synthetic approach towards thiazolo [5,4-d] thiazoles represents a more straightforward route, according to the Ketcham cyclocondensation. Proceeding with the Ketcham process is more challenging since it occurs stepwise and the formation of by-products is obvious. Thiazolo [5,4-d]thiazole is a representative of the aromatic heteropentalene with four heteroatoms in the structure—twinned N and S, two for each of the five-membered rings. The synthetic approaches towards those particular heteropentalnes have been chosen as a consequence of our ongoing research dealing with the design, synthesis and applications of substituted furo [3,2-b]pyrroles and thiazolo [5,4-d]thiazole-based derivatives. While the furopyrroles are known for their pharmacological activity, thiazolothiazoles have become of interest to materials science. We are aware that from a “bank” of existing compounds/procedures not all are presented in this review, and we apologise to respective groups whose research have not been objectively included.

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Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Hemetsberger–Knittel and Ketcham Synthesis of Heteropentalenes with Two (1:1), Three (1:2)/(2:1) and Four (2:2) Heteroatoms

et al. 2023

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Synthesis of Pincer type carbene and their Ag(I)-NHC complexes, and their Antimicrobial activities

Türkyılmaz

Ateş

2022

Journal of Sustainable Construction Materials and Technologies

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In this study, theophylline (1) compounds were synthesized with addition of 2-bromoetha-nol, 2-bromoacetamide and methyl-2-bromoacetate to attain symmetric connections to NHCs (2a–c). New complexes containing the symmetric N-heterocyclic carbene (NHC) ligands were synthesized using azolium salts in dimethyl formamide (DMF). After the NHC predecessor compounds reacted with Ag2O, Ag(I)-NHC complexes were synthesized in the following: 7,9-di-(2-hydroxyethyl)-8,9-dihydro-1,3-dimethyl-1H-purine-2,6(3H,7H)-dionedium silver(I)bromide (3a), 7,9-di(acetamide)-8,9-dihydro-1,3-dimethyl-1H-purine-2,6(3H,7H)-di-ondium silver(I)bromide (3b) and 7,9-di(methylacetate)-8,9-dihydro-1,3-dimethyl-1H-pu-rine-2,6(3H,7H)-diondiumsilver(I)bromide (3c). Both synthesized NHC predecessors (2a-c) and Ag(I)-NHC complexes (3a-c) were described by FTIR, 1H-NMR, 13C-NMR, liquid and solid-state conductivity values, TGA analysis, melting point analysis and XRD spectroscopy. In-vitro antibacterial activities of NHC-predecessors and Ag(I)-NHC complexes were tested against gram-positive bacteria (Staphylococcus Aureus and Bacillus Cereus), gram-negative bacteria (Escherichia Coli and Listeria Monocytogenes), and fungus (Candida Albicans) in Tryptic Soy Broth method. Ag(I)-NHC complexes showed higher antibacterial activity than pure NHC predecessors. The lowest microbial inhibition concentration (MIC) value of compound 3a was obtained as 11.56 μg/ml for Escherichia Coli and 11.52 μg/ml for Staphylococcus Aureus. All tested complexes displayed antimicrobial activity with different results.

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Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Four Extra Heteroatoms 2:2

Cited by 2 publications

References 188 publications

Hemetsberger–Knittel and Ketcham Synthesis of Heteropentalenes with Two (1:1), Three (1:2)/(2:1) and Four (2:2) Heteroatoms

Hemetsberger–Knittel and Ketcham Synthesis of Heteropentalenes with Two (1:1), Three (1:2)/(2:1) and Four (2:2) Heteroatoms

Synthesis of Pincer type carbene and their Ag(I)-NHC complexes, and their Antimicrobial activities

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