Article
Chemistry, Multidisciplinary
Liping Ye, Qian Miao
Summary: New molecular scaffolds with C-, Z-, and box-shaped configurations were synthesized by combining phenazine and pyrene units with oxanorbornene. X-ray crystallography revealed that the C-shaped molecules showed two unique π-π stacking modes of phenazine depending on substituent groups, while the box-shaped molecule formed hydrogen bonds with four chloroform molecules and accommodated two more chloroform molecules in the cavity. The pair of diastereomeric C- and Z-shaped molecules exhibited similar charge transfer absorption and emission, indicating that the intramolecular charge transfer between pyrene (p-donor) and phenazine (p-acceptor) was not affected by the overall molecular geometry.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Changtong Zhu, Zhenbo Yuan, Zhiwei Deng, Dejing Yin, Yan Zhang, Jingwen Zhou, Yijian Rao
Summary: By engineering the enzyme GluER and combining it with photoenzymatic synthesis, the efficient asymmetric synthesis of oxygen-containing benzo-fused heterocycles has been achieved, providing a green approach for the synthesis of important chiral motifs in pharmaceuticals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yanfeng Gao, Hui Wang, Xiaoquan Chen, Yiyang Qiao, Zhiwei Miao
Summary: We present a highly efficient and diastereoselective gold and palladium sequential relay catalysis system for the synthesis of furan-fused eight-membered heterocycles. By utilizing a one-pot procedure, readily available enynamides undergo cyclization to generate azadienes in situ, which then engage in diastereoselective formal[4 + 4] cycloadditions with gamma-methylene-delta-valerolactones. This method enables the rapid and efficient construction of a range of furan-fused azacyclooctanes with diverse substituents in good yields (63-97%) and a high level of diastereoselectivity (7:1 → 20:1 dr).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Min Gao, Yanshu Luo, Qianlan Xu, Yukun Zhao, Xiangnan Gong, Yuanzhi Xia, Lin Hu
Summary: The research achieved a unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides using a chiral phase-transfer catalyst (PTC). This method provides a distinct way to access valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. The DFT calculations were performed to rationalize the high enantioselectivity observed in the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Enrico Marcantonio, Claudio Curti, Lucia Battistini, Andrea Sartori, Luana Cardinale, Giorgio Pelosi, Franca Zanardi
Summary: The remote enolization strategy, strategic exploitation of noncovalent bifunctional organocatalysis, and efficient stereoselective trapping of dienolate intermediates with nitroolefins led to the successful synthesis of functionalized, chiral carbocycle-fused uracils with three contiguous stereocenters in one step, showing good levels of enantioselectivity and complete diastereocontrol. Furthermore, the enantiopure products could be obtained via simple one-cycle recrystallizations and the scaffolds could be further functionalized without losing their chiral integrity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Weinan Chen, Si Liu, Yingjian Ren, Shoudong Xie, Chuan Yan, Zhanglang Zhou, Gang Zhou
Summary: Three S-fused PAHs with cyclopenta[b]thiopyran moieties were successfully synthesized and showed significant halochromic properties. The longest PAH exhibited absorption onset at 1110 nm and was selectively protonated by stronger acid. The non-emissive S-fused PAHs showed strong fluorescence after protonation, which violated the Kasha's rule.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Jinhang Yu, Mengjiao Xu, Xinyuan Wang, Bei Zhang, Hui Mao, Xin Lv, Liejin Zhou
Summary: A novel catalyst-controlled reaction is reported, which allows for the rapid and efficient synthesis of a series of bicyclic compounds by using readily available acyclic enyne-amides and crotonate-derived sulfur ylides as substrates.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Inorganic & Nuclear
Olaya Bernardo, Silvia Gonzalez-Pelayo, Luis A. Lopez
Summary: The marriage of heterocyclic compounds with ferrocene has been a fruitful field of research, with several ferrocene-embedded heterocyclic compounds reported in recent years. The synergistic combination of properties from both heterocyclic and metallacyclic motifs in fused systems has led to interesting applications, particularly in asymmetric catalysis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mengna Zhao, Qian Miao
Summary: The B3N6-[4]triangulene, a key structural unit of BC4N, was successfully synthesized through nitrogen-directed borylation, showing hydrogen-bonding properties. Its slightly bent triangular polycyclic framework consists of 4 pi-electron N-B-N units and forms hydrogen bonds with other molecules like halide or carboxylate anions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Evgeny B. Ulyankin, Anastasia S. Kostyuchenko, Sergey A. Chernenko, Mikhail O. Bystrushkin, Anna L. Samsonenko, Anton L. Shatsauskas, Alexander S. Fisyuk
Summary: A new approach based on iodine-promoted photocyclization was developed for the synthesis of fused benzothiophene derivatives, providing an efficient method compared to traditional oxidative coupling and palladium-catalyzed intramolecular arylation. This method allows for the synthesis of a variety of functionally substituted fused heterocycles containing pyridine and carbazole moieties.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Binbin Ming, Chuan Yan, Shoudong Xie, Si Liu, Yingjian Ren, Hao Zong, Weinan Chen, Gang Zhou
Summary: In this study, a series of thiepine-containing polycyclic S-heterocycles were synthesized via different methods, improving the thermal stability of the thiepine derivatives. Nucleus-independent chemical shift calculations revealed aromatic and nonaromatic characteristics of the incorporated thiopyran and thiepine rings, respectively. The findings provide a facile synthetic methodology for S-fused multi-membered polycyclic heterocycles and a novel construction strategy for thermally stable thiepine derivatives.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Hironobu Nakazawa, Akinobu Ohya, Yuto Morimoto, Yuta Uetake, Naohiko Ikuma, Kenji Okada, Masayoshi Nakano, Yumi Yakiyama, Hidehiro Sakurai
Summary: Sumanene derivatives fused by quinones and acenes were successfully synthesized and exhibited one-dimensional columnar stackings in their structure. These derivatives demonstrated higher solubility and significant stability against oxidation.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Yunlong Zhu, Cheng Qu, Jianjiang Ye, Yincai Xu, Zuolun Zhang, Yue Wang
Summary: In this study, TADF compounds with a D-A-type fused-ring core skeleton are developed. The challenging compatibility between a planarized D-A arrangement and the TADF property is achieved through linking the D and A moieties with two oxygen atoms within a six membered ring. These fused-ring compounds show higher performance in terms of photoluminescence spectra and electroluminescent devices.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Biochemistry & Molecular Biology
Karolina Dzedulionyte, Melita Veiksaite, Vit Moravek, Vida Malinauskiene, Greta Rackauskiene, Algirdas Sackus, Asta Zukauskaite, Egle Arbaciauskiene
Summary: A general approach for the synthesis of tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one derivatives was developed. This approach involved a regioselective strategy for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylates followed by ring-opening and cyclisation reactions to yield the target compounds. A straightforward two-step method was also applied to functionalize other derivatives. The structures of the fused heterocyclic compounds were confirmed using spectroscopy techniques.
Article
Chemistry, Medicinal
Muthuraj Prakash, Yukihiro Itoh, Yoshie Fujiwara, Yukari Takahashi, Yuri Takada, Paolo Mellini, Elghareeb E. Elboray, Mitsuhiro Terao, Yasunobu Yamashita, Chika Yamamoto, Takao Yamaguchi, Masayuki Kotoku, Yuki Kitao, Ritesh Singh, Rohini Roy, Satoshi Obika, Makoto Oba, Dan Ohtan Wang, Takayoshi Suzuki
Summary: This study aimed to design novel FTO-selective inhibitors by merging fragments of previously reported FTO inhibitors, resulting in compound 11b selectively inhibiting FTO. Treatment with a prodrug of 11b decreased the viability of acute monocytic leukemia cells, altered the level of the FTO substrate N-6-methyladenosine in mRNA, and induced changes in expression of FTO target genes MYC and RARA.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Anirban Mukherjee, Ritesh Singh, Kishor D. Mane, Gourab Kanti Das
Summary: Pure quantum mechanical calculations were used to determine the regioselectivity under metalloradical catalysis by Co(II)-porphyrin. The study found that regioselectivity is inherent to the aminyl radical generated from the sulfamoyl azide substrate. Different conformations for the transition state were analyzed to find the most stable conformation for preferable selectivity, in agreement with experimental results.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Deblina Roy, Grace Kaul, Abdul Akhir, Ashok Kumar Sharma, Satyen Saha, Sidharth Chopra, Gautam Panda
Summary: A library of diarylmethyl amines targeting ESKAPE bacterial pathogens was synthesized, and compounds with potent antibacterial activity against Gram-positive bacteria were identified. The presence of lipophilic and nitrogenous components was found to be important for antibacterial activity.
Article
Chemistry, Organic
Amit Kumar, Gaurav Sharma, Sanjeev K. Shukla, Gautam Panda
Summary: A tandem reaction involving semipinacol rearrangement and aldehyde arylation or alkylation has been discovered. This reaction allows for the formation of functionalized 1,3-diols bearing three consecutive tertiary stereocenters from various trisubstituted 2,3-epoxy alcohols and Grignard reagents. The resulting 1,3-diols are confirmed to exist in the anti configuration.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Amit Kumar, Neetu Kumari, Sandeep Bhattacherjee, Umamageswaran Venugopal, Shahid Parwez, Mohammad Imran Siddiqi, Manju Y. Krishnan, Gautam Panda
Summary: Novel chemical compounds were discovered to inhibit the bc1 complex mutant of Mycobacterium tuberculosis, with two molecules showing MICs of 8 and 16 mu M, compared to MICs of 128 and 256 mu M against the wild type. These compounds were bactericidal to wild type bacteria under hypoxic conditions at concentrations much lower than their MICs, and showed synergy with an inhibitor of the bc1 complex in inhibiting bacterial growth.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Review
Chemistry, Organic
Deeksha, Ritesh Singh
Summary: Aza-oxyallyl cations have diverse reactivity profiles for constructing N-scaffolds of biological interest and recent studies have reported new variations in their reactivity, making them versatile tools for organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kasim Ali, Gautam Panda
Summary: An efficient transition-metal-free multicomponent approach to the regioselective synthesis of highly substituted N-alkylpyrazoles through 1,6-addition of pyrazole (in situ generated from alpha,beta-unsaturated aldehyde and hydrazide) to para-Quinone Methides has been developed. The N-alkylpyrazole containing triarylmethanes having several heteroaryl rings (quinoline, pyridine, thiophene) at the central methine carbon atom was developed. This chemical process may be used for large-scale synthesis and provides a novel way to produce triarylmethanes with diverse functional groups.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Review
Chemistry, Medicinal
Indranil Chatterjee, Kasim Ali, Gautam Panda
Summary: This review critically analyzes the synthetic strategies and anticancer activities of benzoxazines and benzoxazepines compounds reported from 2010 onwards. The structure-activity relationship of the benzoxazine and benzoxazepine scaffolds containing bioactive compounds is also studied, focusing on how structural modification affects their anticancer activity.
Review
Chemistry, Multidisciplinary
Arpita Banerjee, Indranil Chatterjee, Gautam Panda
Summary: This article discusses the significance of tyrosine as a chiral pool in the synthesis of alkaloids, and compares synthetic steps, overall yield, and other factors between tyrosine-based and non-tyrosine-based routes.
Article
Chemistry, Multidisciplinary
Saroj Maji, Souvik Barman, Gautam Panda
Summary: In this study, a novel synthetic route towards nintedanib was developed using a stereoselective intramolecular cyclization strategy to convert beta-keto amide into a 3-acyloxindole derivative, an important scaffold for nintedanib synthesis. The condensation of the oxindole scaffold with a synthesized amine derivative led to the successful synthesis of nintedanib.
Article
Chemistry, Organic
Indranil Chatterjee, Gautam Panda
Summary: This paper describes a palladium-catalyzed regioselective reaction of propargylic carbonate with thiophenols and benzene selenol. The addition of thiols to propargylic carbonates provides an atom-economic and effective process. The reaction proceeds through hydrothiolation to produce mono(arylthiol) alkenes and hydrothiolation followed by Tsuji-Trost type substitution to form bis(arylthiol) alkenes by controlling the equivalence of thiophenols. This coupling reaction exhibits good tolerance towards functional groups and leads to the formation of highly functionalized alkenylation products via the formation of new C-S and C-Se bonds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Indranil Chatterjee, Gautam Panda
Summary: A simple and efficient metal-free approach was developed for synthesizing 4-thio-substituted chroman and diarylmethyl thioethers, providing good yields and tolerance for labile functional groups. This method is applicable to large-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kasim Ali, Gurudayal Prajapati, Ravi Sankar Ampapathi, Gautam Panda
Summary: The reductive coupling between allylic sulfonylhydrazones and aryl boronic acids can efficiently generate 1,3-diarylpropene systems under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Arpita Banerjee, Gautam Panda
Summary: In this study, a base mediated, transition metal-free intermolecular epoxide ring opening reaction followed by intramolecular aromatic nucleophilic substitution (SNAr) was developed to synthesize separable diastereomers of selected benzo[b][1,4,5]oxathiazepine 1-oxides. This strategy allows the formation of both C-N and C-O bonds simultaneously in a single step. The method has a wide substrate scope, uses simple reaction conditions, and is applicable for synthesizing bioactive molecules with similar skeletons as benzoxathiazepine 1-oxides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Kasim Ali, Prajjval Mishra, Awnish Kumar, Damodara N. Reddy, Sushobhan Chowdhury, Gautam Panda
Summary: In this article, the synthesis, structure-reactivity relationships, and synthetic applications of quinone methides are discussed. The formation of intermediates during bioactivation and potential chemical manifestations leading to toxicity in biological systems are also covered.
CHEMICAL COMMUNICATIONS
(2022)
