Article
Chemistry, Organic
Shan-Shan Li, Qi Qin, Zhuang Qi, Li-Miao Yang, Yun Kang, Xiang-Zhi Zhang, Ai-Jun Ma, Jin-Bao Peng
Summary: An efficient synthesis of disubstituted gamma-butyrolactones and spirocyclopropanes has been developed via a multicomponent reaction of aldehydes, Meldrum's acid, and sulfoxonium ylides. Different types of aromatic and aliphatic aldehydes led to the formation of different products under mild conditions. The cyclopropane intermediate can be converted to gamma-butyrolactone under Lewis acid conditions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Ramu Sridhar Perali, Umamaheswara Rao Boddu, Drisya Chittadi Sankar
Summary: The study presents a simple and efficient strategy for the regio- and stereoselective synthesis of carbon-branched sugar derivatives. By implementing Wittig rearrangement on substrates derived from various glycals and 3-O-alkenyl glycals through Ferrier rearrangement, a highly selective [1,2]- or [2,3]-Wittig rearrangement is revealed, providing a novel class of stereodefined 3-C-branched glycals and C-glycosides that are otherwise difficult to obtain.
Article
Chemistry, Organic
Jing Sun, Xueyan Liu, Qiu Sun, Ying Han, Chao-Guo Yan
Summary: Diverse functionalized dihydrobenzofuran spiro-indanedione scaffolds were synthesized via base-promoted cyclization reaction. The selective synthesis of two diastereomeric dispiro[indene-2,1′-cyclopenta[b]benzofuran-2,3′-indolines] was achieved using DABCO or DMAP as a base promoter. Moreover, DABCO or DMAP facilitated the annulation reaction of MBH formates, resulting in the formation of spiro[cyclopropa[c]chromene-1,2′-indene]-1′,3′-diones or dispiro[indene-2,1′-cyclopenta[b]benzofuran-2,3′-indolines]. Additionally, high-yielding and highly diastereoselective synthesis of dispiro[indene-2,5′-benzofuro[2′,3′:1,5]cyclopenta[1,2-c]pyrrole-4′,3″-indolines] was achieved using MBH maleimides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dan Liu, Xueyan Liu, Jing Sun, Ying Han, Chao-Guo Yan
Summary: The base promoted domino reactions of bindone with common 1,3-dipolarophiles resulted in the synthesis of diverse molecules, including unique spiro and fused indeno[1,2-a]fluorine derivatives. Triethylamine promoted reactions of 1,3-indanediones and isatins also led to the formation of spiro[diindeno[2,1-b:2',1'-d]anthracene-11,3'-indoline] derivatives through a domino [4 + 2] cycloaddition and ring-expansion process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Suven Das, Arpita Dutta
Summary: This review focuses on recent advancements in the cyclization reactions of 1-indanones, specifically on the construction of fused- and spirocyclic frameworks. New synthetic strategies for the synthesis of various carbocyclic and heterocyclic skeletons are demonstrated. The review also highlights the formation of biologically relevant compounds and natural products.
Article
Chemistry, Physical
Paul M. DeMent, Chenlu Liu, Joseph Wakpal, Richard N. Schaugaard, H. Bernhard Schlegel, Hien M. Nguyen
Summary: Phenanthroline is a commonly used bidentate ligand in coordination chemistry, which can be tuned to develop efficient and stereoselective catalysts. By activating 2-deoxy-2-fluoro glycosyl halides with phenanthroline-based catalysts, glycosylations with high levels of alpha-selectivities and moderate to high yields can be achieved. The proposed mechanism for this catalytic glycosylation system involves double S(N)2 displacement pathways with phenanthroline catalysts, ensuring stereoselective formation of alpha-1,2-cis-2-fluoro glycosides.
Article
Chemistry, Multidisciplinary
Eva Juhasz-Toth, Adam Szilard Malecz, Marietta Toth, Agnes Homolya, Timea Kaszas, Laszlo Somsak, Laszlo Juhasz
Summary: A series of iodo-glycals with electron withdrawing groups were synthetized and demonstrated to react with boronic acids through Suzuki-Miyaura coupling reactions, yielding 1,2-C,C-disubstituted glycals.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaofei Yi, Zongxiang Zhao, Manman Wang, Wenquan Yu, Junbiao Chang
Summary: In this study, an intramolecular sp3 C-H amination reaction of aniline derivatives was established using molecular iodine under transition-metal-free conditions. The reaction yielded 1,2-fused or 1,2-disubstituted benzimidazoles in an efficient and scalable fashion. This synthetic process also produced novel benzimidazolium frameworks and bioactive compounds.
Review
Chemistry, Organic
Americo J. S. Alves, Nuno G. Alves, Maria I. L. Soares, Teresa M. V. D. Melo
Summary: Spiro-gamma-lactams are a class of spirocyclic compounds found in synthetic bioactive and naturally occurring molecules, with increasing interest in their synthesis as synthetic building blocks in organic chemistry. Recent advances in the synthesis of the spiro-gamma-lactam scaffold since 2015 have addressed issues such as scope, efficiency, selectivity, and mechanistic insights.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Christian L. L. Jankovic, Kyle C. C. McIntosh, Verner A. A. Lofstrand, F. G. West
Summary: Mild fluoride-mediated desilylative conditions generate 1,2-cyclohexadienes, which undergo efficient intramolecular [2+2] trapping to form tricyclic alkylidene cyclobutanes with complete diastereoselectivity for the cis-fused products. These cyclohexadienes can be trapped by pendent styrenes or electron-deficient olefins, and 14 substrates have been disclosed. The reactions achieve yields up to 91% at ambient temperature using only cesium fluoride and the necessary precursors are easily accessible from substituted 2-bromocyclohexenones.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Shilpi Gupta, Smritilekha Bera, Dhananjoy Mondal
Summary: The synthesis of conformationally constrained non-anomeric furanoid sugar quaternary alpha-amino acids and sugar fused 6-and gamma-lactones from D-glucose has been achieved. The furanoid sugar alpha-amino acids were obtained by introducing amine and nitrile functionality at the C-3 position of glucose, generating the aminonitrile derivative as a single diastereomer. The Pinner cyclisation of the C-6 primary hydroxy of amino nitrile derivative led to the formation of glucose-fused 6-lactone. Basic hydrolysis of these sugar lactones and subsequent reactions yielded sugar-fused gamma-lactone, as well as sugar-templated aspartic acid, keto-functionalized glutamic acid, and homoserine.
Review
Chemistry, Organic
Suven Das
Summary: 3-nitrochromenes, as an important class of organic compounds, have been attracting attention due to their easy availability and versatile reactivity for constructing complex molecular architectures. This review highlights recent advances (2017-2021) in the synthesis of various fused- and spiro scaffolds involving 3-nitrochromene derivatives, focusing on their reaction mechanisms and promising biological activities.
SYNTHETIC COMMUNICATIONS
(2022)
Review
Chemistry, Organic
Shrestha Chatterjee, Rajkumar Sahoo, Samik Nanda
Summary: Gamma-butenolides are fundamental structures found in many natural compounds with significant biological activities. Synthetic chemists have focused on developing strategies for optically active gamma-butenolides, particularly emphasizing metal-mediated catalytic transformation and organocatalysis. This report discusses isolation, biogenesis, and state-of-the-art synthetic protocols for gamma-butenolides from 2010-2020, with a focus on gamma-alkylidenebutenolides and related molecules.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Maruti B. Yadav, Sandip S. Vagh, Yeon Tae Jeong
Summary: An efficient method for constructing spiro[indoline-pyran] and fused (epoxyetheno)indeno[1,2-b]furan compounds has been developed from 1-cyanoketones and 1,2-diketones through Knoevenagel and Michael adduct reactions. This synthesis allows for the preparation of heterocyclic compounds with one or more tetra-substituted carbon centers and sequential hexa- and penta-cyclic core under mild conditions, showing excellent chemo and regioselectivity. Additionally, the synthesis was demonstrated on a gram scale.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Ruby Singh, Diksha Bhardwaj, Munna Ram Saini
Summary: The nitrogen-containing indeno[1,2-b]quinoxaline ring is recognized as an important building block in organic synthesis and has notable applications. Various chemical reactions using indeno[1,2-b]quinoxalinone have been summarized here to produce diverse spiro-heterocyclic frameworks, some of which exhibit interesting biological activities. These spiro-indenoquinoxalines are promising in drug discovery due to their unique structural features and potential pharmaceutical applications.
Article
Polymer Science
S. N. Raju Kutcherlapati, Niranjan Yeole, Madhusudhan Reddy Gadi, Ramu Sridhar Perali, Tushar Jana
Article
Chemistry, Multidisciplinary
Shuaishuai Wang, Qing Zhang, CongCong Chen, Yuxi Guo, Madhusudhan Reddy Gadi, Jin Yu, Ulrika Westerlind, Yunpeng Liu, Xuefeng Cao, Peng G. Wang, Lei Li
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Review
Chemistry, Multidisciplinary
Liuqing Wen, Garrett Edmunds, Christopher Gibbons, Jiabin Zhang, Madhusudhan Reddy Gadi, Hailiang Zhu, Junqiang Fang, Xianwei Liu, Yun Kong, Peng George Wang
Article
Chemistry, Physical
Liuqing Wen, Madhusudhan Reddy Gadi, Yuan Zheng, Christopher Gibbons, Shukkoor Muhammed Kondengaden, Jiabin Zhang, Peng George Wang
Article
Chemistry, Multidisciplinary
Jiabin Zhang, Congcong Chen, Madhusudhan Reddy Gadi, Christopher Gibbons, Yuxi Guo, Xuefeng Cao, Garrett Edmunds, Shuaishuai Wang, Ding Liu, Jin Yu, Liuqing Wen, Peng G. Wang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Biochemistry & Molecular Biology
Jing Bai, Zhigang Wu, Go Sugiarto, Madhusudhan Reddy Gadi, Hai Yu, Yanhong Li, Cong Xiao, Alice Ngo, Baohua Zhao, Xi Chen, Wanyi Guan
CARBOHYDRATE RESEARCH
(2019)
Article
Chemistry, Organic
Perali Ramu Sridhar, Boddu Umamaheswara Rao, Gadi Madhusudhan Reddy
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Medicinal
Zhongrui Ma, Gao-Lan Zhang, Madhusudhan Reddy Gadi, Yuxi Guo, Peng Wang, Lei Li
ACS INFECTIOUS DISEASES
(2020)
Article
Biochemistry & Molecular Biology
Ding Liu, Jiabin Zhang, He Zhu, Mingzhang Wang, Samuel Justin Polizzi, Michael T. Jones, Lei Li, Madhusudhan Reddy Gadi, Peng George Wang, Cheng Ma, Wei Huang
CARBOHYDRATE RESEARCH
(2020)
Article
Chemistry, Multidisciplinary
Jiabin Zhang, Ding Liu, Varma Saikam, Madhusudhan R. Gadi, Christopher Gibbons, Xuan Fu, Heliang Song, Jin Yu, Shukkoor M. Kondengaden, Peng G. Wang, Liuqing Wen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Gao-Lan Zhang, Madhusudhan Reddy Gadi, Xikai Cui, Ding Liu, Jiabin Zhang, Varma Saikam, Christopher Gibbons, Peng G. Wang, Lei Li
Summary: The facile and green S-glycosylation method developed utilizes Ca(OH)(2) as a promoter to achieve high-yield synthesis of various thioglycosides with exclusive stereoselectivity. Additionally, it enables successful production of S-linked oligosaccharides and S-linked glycopeptides.
Correction
Chemistry, Multidisciplinary
Gao-Lan Zhang, Madhusudhan Reddy Gadi, Xikai Cui, Ding Liu, Jiabin Zhang, Varma Saikam, Christopher Gibbons, Peng G. Wang, Lei Li
Summary: The study presents a protection-group-free method for S-glycosylation, which can be applied in the synthesis of thioglycosides and thioglycopeptides in water.
Article
Chemistry, Multidisciplinary
Congcong Chen, Shuaishuai Wang, Madhusudhan Reddy Gadi, He Zhu, Fei Liu, Chang-Cheng Liu, Lei Li, Fengshan Wang, Peixue Ling, Hongzhi Cao
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Hai Yu, Yanhong Li, Zhigang Wu, Lei Li, Jie Zeng, Chao Zhao, Yijing Wu, Nova Tasnima, Jing Wang, Huaide Liu, Madhusudhan Reddy Gadi, Wanyi Guan, Peng G. Wang, Xi Chen
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Medicinal
Hailiang Zhu, Zhigang Wu, Madhusudhan Reddy Gadi, Shuaishuai Wang, Yuxi Guo, Garrett Edmunds, Wanyi Guan, Junqiang Fang
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
