1333395-36-0Relevant articles and documents
A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones
Wang, Wei-Feng,Peng, Jin-Bao,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
, p. 3521 - 3524 (2019/02/14)
A convenient palladium-catalyzed carbonylation reaction for the efficient synthesis of (E)-3-benzylidenechroman-4-ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)-3-benzylidenechroman-4-ones were prepared in moderate to good yields with 2-iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin-4(1H)-ones can also be obtained with 2-iodoaniline as the starting material.
Synthesis and SAR study of new hydroxy and chloro-substituted 2,4-diphenyl 5H-chromeno[4,3-b]pyridines as selective topoisomerase IIα-targeting anticancer agents
Magar, Til Bahadur Thapa,Seo, Seung Hee,Kadayat, Tara Man,Jo, Hyunji,Shrestha, Aarajana,Bist, Ganesh,Katila, Pramila,Kwon, Youngjoo,Lee, Eung-Seok
, p. 1909 - 1919 (2018/03/07)
As part of our effort to develop potential topoisomerase IIα (topo IIα) targeting anticancer agents, we systematically designed a new series of hydroxy and chloro-substituted 2,4-diphenyl 5H-chromeno[4,3-b]pyridines. Total eighteen compounds were synthesi
Synthesis of rigid analogues of flavone by intramolecular heck reaction
Hou, Chuanwei,Chen, Hao,Xu, Xing,Zhu, Fangxia,Guo, Lei,Jiang, Min,Yang, Chunhao,Deng, Lianfu
supporting information, p. 3040 - 3043 (2015/05/13)
A novel concise method to synthesize rigid analogues of flavone by an intramolecular Heck reaction with wide substrate scope was developed. The key intermediates 3-(2-bromobenzyl)-4H-chromen-4-ones were prepared easily in two steps. Most compounds were obtained with moderate to good yields (34-90?% yield, 19 examples). As the title reaction shows, rigid analogues of flavone were synthesized by an intramolecular Heck reaction from 3-(2-bromobenzyl)-4H-chromen-4-ones, which could be prepared easily in two steps. Most compounds were obtained with moderate to good yields.
Topochemical photodimerization of (E)-3-benzylidene-4-chromanone derivatives from β-type structures directed by halogen groups
Cheng, Xue-Ming,Huang, Zhi-Tang,Zheng, Qi-Yu
experimental part, p. 9093 - 9098 (2011/12/01)
Halogen substituent plays an important role in the crystalline packing of aromatic compounds. The [2+2] photocycloaddition of (E)-3-benzylidene-4- chromanones in the crystalline state was investigated, and halogen substitution has been adopted to organize molecules with proper arrangement for photodimerization. Not halogen bonds, but the electron-withdrawing property of halogen atoms can enhance the face-to-face π-π interactions. Therefore, F, Cl or Br substitution at the para position of phenyl gave rise to almost the same β-structures with face-to-face π-stacking. Only resulted β-structures can undergo photodimerization, which gave the syn-HH (syn-head-to-head) products with high regio-/stereoselectivity.
Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1-benzopyran-4-ones which display selective toxicity for malignant cells
Perjesi, Pal,Das, Umashankar,De Clercq, Erik,Balzarini, Jan,Kawase, Masame,Sakagami, Hiroshi,Stables, James P.,Lorand, Tamas,Rozmer, Zsuzsanna,Dimmock, Jonathan R.
, p. 839 - 845 (2008/09/20)
A series of 3-benzylidene-4-chromanones 1a-l were prepared and their cytotoxicity towards human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 lymphoid leukemia cells were compared to the previously generated biodata in these three assays for the
Etude RMN(1)H et radiocristallographique de la stereochemie de 3-aryl-9b-hydroxy-1,3,3a,9b-tetrahydro-4H-thienobenzopyrane-1-carboxylates d'ethyle. Configuration et conformation
Alhassan, M.,Robert, J. F.,Xicluna, A.,Ombetta, J. E.,Mercier, R.,Laude, B.
, p. 1109 - 1120 (2007/10/02)
The reaction of ethyl mercaptoacetate with some 3-arylidene-4-chromanones yields the corresponding ethyl 3-aryl-9b-hydroxy-1,3,3a,9b-tetrahydro-4H-thienobenzopyrane-1-carboxylates.In spite of the presence of four chirality centers, the reaction is diastereospecific and gives a single diastereoisomer whose configuration and conformation were specified by its PMR data.The cis-fused tetrahydrothiophenic and dihydropyranic cycles lie in half-chair conformation.The 9b-hydroxyl and the 3-aryl groups are in a cis equatorial and pseudoequatorial disposition.The ester group, also cis with the hydroxyl group, presents a hydrogen bond with the hydroxyl.In the presence of an ortho-substituent at the phenyl group (particularly a chlorine atom), this phenyl group undergoes a notable rotation as is pointed out by a radiocristallographic study.A comparative study between the NMR and radiogcristallographic data allows the confirmation of the maintenance of the same conformation in solid and dissolved states.
Stereochemical studies of Michael-adducts obtained by reaction of the ethyl mercaptoacetate with substituted 3-benzylidenchroman-4-ones and of their cyclization into 4H-thienobenzopyran derivatives.
Robert, JF.,Alhassan, M.,Xicluna, A.,Ombetta, JE.,Mercier, MF.,et al.
, p. 788 - 797 (2007/10/02)
The reaction of ethyl mercaptoacetate with substituted 3-benzylidenechroman-4-ones gives mixtures of erythro and threo diastereoisomers.In one case, the erythro-isomer was isolated and its structure specified by NMR and crystallographic studies.These studies allow us to analyse the mixtures of the other Michael adducts.The erythro-isomer does not cyclize directly but via an epimerization into the threo-isomer.This occurs under the influence of a basic reagent such as piperidine and gives a single diastereoisomer of a 4H-thienobenzopyran derivative.On the basis of the Cram, Felkin and Bassindale models, we propose a chelated transition state to explain both the remarkable stereoselectivity of the cyclization reaction and why it does not occur in the case of the Michael adduct issued from 3-ortho-nitrobenzylidenechroman-4-one. - - - 3-benzylidenechroman-4-ones / stereochemistry / stereoselectivity / 1H NMR spectroscopy / Michael adducts / 4-H-thienobenzopyran
