56074-73-8Relevant academic research and scientific papers
A Base-Catalyzed, Domino Aldol/hetero-Diels-Alder Synthesis of Tricyclic Pyrano[3,4-c]chromenes in Glycerol
Parmar, Bhagyashri D.,Sutariya, Tushar R.,Brahmbhatt, Gaurangkumar C.,Parmar, Narsidas J.,Kant, Rajni,Gupta, Vivek K.
, p. 4955 - 4964 (2016)
The domino aldol/hetero-Diels-Alder synthesis of some new tricyclic pyrano[3,4-c]chromene derivatives has been achieved successfully after assembling a variety of acyclic or cyclic monoketones with prenyl ether-tethered aldehydes in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in glycerol at 120 °C. The hitherto unreported stereochemical outcome of this synthetic sequence was studied and established on the basis of single-crystal X-ray diffraction data and 2D NMR NOESY spectroscopy along with the isolation and characterization of the intermediate Aldol condensation product.
Synthesis and antifungal activity of polycyclic pyridone derivatives with anti-hyphal and biofilm formation activity against Candida albicans
Kamauchi, Hitoshi,Kimura, Yu,Seki, Taishi,Sugita, Yoshiaki,Suzuki, Mitsuaki,Takao, Koichi,Ushiwatari, Mikoto
supporting information, (2021/02/26)
Thirty-five pyridone derivatives were synthesized, with derivatization conducted on polycyclic pyridone scaffolds, including cis- or trans-oxydecalin and other cyclic structures, by domino-Knoevenagel-electrocyclic reactions. The anti-fungal activities of the synthesized compounds were tested against Candida albicans. Ten compounds inhibited hyphal formation without inhibiting growth. Pyridones with anti-hyphal formation activity (4c, 6d, 12a and 12c) were tested for their ability to inhibit biofilm formation. Compound 6d showed both anti-hyphal and biofilm inhibition activity.
Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis
Haun, Graham,Paneque, Alyson N.,Almond, David W.,Austin, Brooke E.,Moura-Letts, Gustavo
supporting information, p. 1388 - 1392 (2019/03/08)
This effort reports the first redox-neutral visible-light photocatalytic intramolecular dipolar cycloaddition for the diastereoselective synthesis of chromenoisoxazolidines. The authors have found that alkenylphenyl nitrones with a diverse substitution pattern on the aromatic ring and the alkenyl substituent undergo visible-light-promoted cycloadditions in the presence of catalytic amounts of Ru(bpy)3Cl2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.
A nickel(ii)-catalyzed asymmetric intramolecular Alder-ene reaction of 1,7-dienes
Liu, Wen,Zhou, Pengfei,Lang, Jiawen,Dong, Shunxi,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 4479 - 4482 (2019/04/26)
A highly diastereo- and enantioselective intramolecular Alder-ene reaction with an alkene as the enophile has been developed by using a chiral N,N′-dioxide/nickel(ii) complex as the catalyst. This protocol provides a facile route towards the synthesis of diverse 3,4-disubstituted chroman, tetrahydroquinoline, piperidine and thiochroman derivatives in high yields with good to excellent diastereo- and enantioselectivities.
Tetrahydrobenzochromene Synthesis Enabled by a Deconjugative Alkylation/Tsuji-Saegusa-Ito Oxidation on Knoevenagel Adducts
Navaratne, Primali V.,Grenning, Alexander J.
supporting information, p. 4566 - 4570 (2018/08/09)
A modular and practical route to versatile cyano-1,3-dienes by a sequence involving deconjugative alkylation and "Tsuji-Saegusa-Ito oxidation" is reported. In this letter, the versatility of the products is also explored, including a route to benzochromene scaffolds common to many natural products.
Hydrazone–Cu-Catalyzed Suzuki–Miyaura-Type Reactions of Dibromoalkenes with Arylboronic Acids
Watanabe, Kohei,Mino, Takashi,Hatta, Chikako,Ishikawa, Eri,Yoshida, Yasushi,Sakamoto, Masami
supporting information, p. 3612 - 3619 (2017/07/22)
We have found that Suzuki–Miyaura-type reactions of dibromoalkenes with arylboronic acids using a hydrazone–Cu catalyst system proceeded smoothly under mild conditions to afford the corresponding internal alkyne derivatives in good yields. Furthermore, we also succeeded in the synthesis of o-allyloxy(ethynyl)benzene derivatives, which are known to be effective precursors of various heterocyclic compounds, through this reaction.
One-pot synthesis, biological evaluation, and docking study of new chromeno-annulated thiopyrano[2,3-c]pyrazoles
Parmar, Bhagyashri D.,Sutariya, Tushar R.,Brahmbhatt, Gaurangkumar C.,Parmar, Narsidas J.,Kant, Rajni,Gupta, Vivek K.,Murumkar, Prashant R.,Sharma, Mayank Kumar,Yadav, Mange Ram
, p. 639 - 657 (2016/07/12)
Abstract: A one-pot synthesis of new chromeno-annulated thiopyrano[2,3-c]pyrazoles has been achieved through a domino-Knoevenagel–hetero-Diels–Alder reaction after combining various pyrazol-5-thiones with O-alkenyloxy/alkynyloxy-salicylaldehydes/naphthaldehydes in a Br?nsted acidic ionic liquid, [Hmim]HSO4, methylimidazolium hydrogen sulphate, under microwave irradiation. The method is simple and in many cases the isolated products did not require further purification. The central pyranothiopyranyl cis-fusion was confirmed by 2D NMR NOESY and single-crystal X-ray analysis suggesting that the endo-E-Syn transition state would be the most favored pathway of the reaction. Many heterocycles of this new series were found active against six bacterial and two fungal strains. In addition, all the compounds possess good anti-oxidant activity with the ferric reducing anti-oxidant power value >100mmol/100g. All new structures were docked into active site of angiotensin I converting enzyme (ACE), assuming that the compounds possessed the anti-hypertensive activity potential on the basis of prediction of activity spectra of substances prediction results. Pyranyl ring oxygen in compound 9a forms two hydrogen bonds with HIS353 and HIS513 residues in the active site of the ACE having good G score (- 4.06) of this compound, comparable to that of the reference drug captopril (- 4.93). Graphical Abstract: [Figure not available: see fulltext.]
Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones
Schmidt, Bernd,Riemer, Martin,Schilde, Uwe
supporting information, p. 7602 - 7611 (2016/01/25)
Allyl, dimethylallyl and prenyl ethers derived from o-acylphenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.
An efficient synthesis of some thiopyranopyrazole-heterocycles via domino reaction in a Bronsted acidic ionic liquid
Parmar, Narsidas J.,Parmar, Bhagyashri D.,Sutariya, Tushar R.,Kant, Rajni,Gupta, Vivek K.
supporting information, p. 6060 - 6064 (2015/01/08)
The thiopyrazole gave many new polycyclic thiopyranopyrazole-heterocycles when it was assembled with a variety of O-alkenylated/alkynylated salicylaldehydes and naphthaldehydes in Bronsted acidic ionic liquid, [Hmim]HSO4, via domino/Knoevenagel-hetero-Diels-Alder (DKHDA) reaction. The reaction is highly stereoselective and the work-up procedure required no chromatography of products in many cases.
