- SUBSTITUTED CHROMANES, ANALOGS THEREOF, AND METHODS OF USE AND SYNTHESIS
-
Disclosed are chromane compounds, analogs thereof, and methods of their synthesis and use. The compounds may be synthesized by methods involving reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis. The compounds may be formulated in a pharmaceutical composition for treating one of the aforementioned diseases or disorders.
- -
-
Paragraph 0162; 0198; 0200; 0202
(2021/01/25)
-
- Copper(I)-Catalyzed Intramolecular Cyclization of o-Propargyloxy Diketopiperazines to Access Diverse Diazabicyclic and Spiro-Diketopiperazinochromanes
-
In this report, two distinctive intramolecular cyclizations of o-propargyloxy diketopiperazines (achieved from a one-pot Ugi post-transformation) is achieved via a copper(I)-catalyzed intramolecular reaction of azomethine ylide and alkyne moiety. The presence of internal alkyne in the starting materials directed the reaction towards through [3+2]-cycloaddition, while terminal alkyne led to a spirocyclization reaction between azomethine ylide and terminal unsaturated C?C bond. This method offering an opportunity for the synthesis of challenging Diazabicyclics and Spiro-Diketopiperazinochromanes in high yields with exclusive diastereoselectivity. (Figure presented.).
- Armaghan, Mahsa,Balalaie, Saeed,Bijanzadeh, Hamid Reza,Frank, Walter,Manavi, Bita,Rominger, Frank,Tejeneki, Hossein Zahedian
-
p. 4190 - 4196
(2021/08/06)
-
- Pyridinium triflate catalyzed intramolecular alkyne-carbonyl metathesis reaction of O-propargylated 2-hydroxyarylaldehydes
-
3,5-Dibromopridinium trifluoromethanesulfonate catalyzes the intramolecular alkyne-carbonyl metathesis reaction of a variety of O-propargylated 2-hydroxyarylaldehydes and ketones bearing alkyl, aryl and heteroaryl substituted internal alkynes to provide v
- Saini, Manoj Kumar,Korawat, Harshita Singh,Verma, Shashi Kant,Basak, Ashok K.
-
supporting information
(2020/12/02)
-
- Direct Access to 9-Chloro-1 H-benzo[ b]furo[3,4- e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade
-
An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.
- Karuppasamy, Muthu,Vachan,Vinoth, Perumal,Muthukrishnan, Isravel,Nagarajan, Subbiah,Ielo, Laura,Pace, Vittorio,Banik, Subrata,Maheswari, C. Uma,Sridharan, Vellaisamy
-
supporting information
p. 5784 - 5788
(2019/08/26)
-
- Straightforward synthesis and biological evaluation as topoisomerase I inhibitors and antiproliferative agents of hybrid Chromeno[4,3-b][1,5]Naphthyridines and Chromeno[4,3-b][1,5]Naphthyridin-6-ones
-
This work describes the synthesis of hybrid tetrahydro-1,5-naphthyridine and 1,5-naphthyridine derivatives fused with heterocycles such as chromenes and chromen-2-ones or coumarins, which were synthesized in good to high general yields. The synthetic rout
- Martín-Encinas, Endika,Rubiales, Gloria,Knudssen, Birgitta R.,Palacios, Francisco,Alonso, Concepción
-
supporting information
p. 752 - 766
(2019/06/24)
-
- Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels-Alder Reaction with O-(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
-
A highly efficient and regioselective approach to new polycyclic embelin derivatives through a domino Knoevenagel condensation/intramolecular hetero Diels-Alder reaction using O-(arylpropynyloxy)-salicylaldehydes in the presence of ethylenediamine diacetate (EDDA) is reported. This organocatalyzed protocol is compatible toward a wide range of aryl-substituted alkynyl ethers with electron-donating and electron-withdrawing groups. When other active methylene compounds were subjected to this domino reaction the corresponding adducts were obtained in high yield.
- Martín-Acosta, Pedro,Feresin, Gabriela,Tapia, Alejandro,Estévez-Braun, Ana
-
p. 9738 - 9756
(2016/11/02)
-
- Intramolecular heterocyclization of o -propargylated aromatic hydroxyaldehydes as an expedient route to substituted chromenopyridines under metal-free conditions
-
A concise and regioselective approach to the synthesis of chromenopyridine and chromenopyridinone derivatives was developed. The synthetic strategy relies on the O-propargylation of aromatic hydroxyaldehydes followed by reaction with propargylamine. The i
- Keskin, Selbi,Balci, Metin
-
supporting information
p. 964 - 967
(2015/03/18)
-
- Base-mediated intramolecular cyclization of (2-propargyl ether) arylimines: An approach to 3-amino-benzofurans
-
We present here a practical synthesis of functional 3-amino-benzofurans through base-promoted intramolecular cyclization of (2-propargyl ether) arylimines. A systematic study of the cyclization system revealed that the presence and the amount of base play
- Gai, Rafaela,Prochnow, Thaís,Back, Davi F.,Zeni, Gilson
-
supporting information
p. 3751 - 3756
(2014/05/20)
-
- Lewis acid-catalyzed intramolecular [3+2] cycloaddition of cyclopropane 1,1-diesters with alkynes for the synthesis of cyclopenta[c]chromene skeletons
-
An efficient method to construct cyclopenta[c]chromene skeletons by Lewis acid-catalyzed intramolecular [3+2] cycloaddition of cyclopropane 1,1-diesters with alkynes is presented. Two new fused cycles can be formed in one step in moderate to excellent yie
- Xia, Xiao-Feng,Song, Xian-Rong,Liu, Xue-Yuan,Liang, Yong-Min
-
supporting information; experimental part
p. 1538 - 1541
(2012/08/08)
-
- Iron-catalyzed synthesis of functionalized 2H-chromenes via intramolecular alkyne-carbonyl metathesis
-
An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, bromo, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.
- Bera, Krishnendu,Sarkar, Soumen,Biswas, Srijit,Maiti, Sukhendu,Jana, Umasish
-
p. 3539 - 3544
(2011/06/23)
-
- Intramolecular Povarov reactions involving 3-aminocoumarins
-
A series of pentacyclic heterocyclic systems (15 examples, 69-89%) have been synthesized using intramolecular Povarov reactions involving 3-aminocoumarins and O-cinnamylsalicylaldehydes. The Povarov adducts are formed with high selectivity for the trans,trans relative stereochemistry in the newly-formed [6,6] fused ring system. One example of a Povarov adduct featuring a new [6,5] fused ring system is reported. In this case, cis,trans relative stereochemistry was preferred.
- Kudale, Amit A.,Miller, David O.,Dawe, Louise N.,Bodwell, Graham J.
-
p. 7196 - 7206
(2011/10/31)
-
- N-heterocyclic carbene-catalyzed cascade reaction involving the hydroacylation of unactivated alkynes
-
The N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated alkynes to provide α,β-unsaturated ketones is reported. In addition, a rare case of an efficient and selective dually NHC-catalyzed cascade reaction involving the hydroacylation of a
- Biju, Akkattu T.,Wurz, Nathalie E.,Glorius, Frank
-
supporting information; experimental part
p. 5970 - 5971
(2010/07/05)
-
- A simple approach to highly functionalized benzo[b]furans from phenols and aryl iodides via aryl propargyl ethers
-
A variety of mono- and disubstituted phenols are alkylated with propargyl bromide to give phenyl 2-propynyl ethers, which were further coupled with aryl iodides under Sonogashira reaction conditions to give 3-phenoxy-1-aryl-1-propyne derivatives. The latt
- Lingam, V.S. Prasada Rao,Vinodkumar, Ramanatham,Mukkanti, Khagga,Thomas, Abraham,Gopalan, Balasubramanian
-
p. 4260 - 4264
(2008/09/21)
-
- Alkynes as synthetic equivalents to stabilized wittig reagents: Intra- and intermolecular carbonyl olefinations catalyzed by Ag(I), BF3, and HBF4
-
(Chemical Equation Presented) The first use of cationic silver (AgSbF 4) as a catalyst for intra- and intermolecular alkyne - carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Bronsted acid (HBF4/
- Rhee, Jong Uk,Krische, Michael J.
-
p. 2493 - 2495
(2007/10/03)
-
- A new method for the synthesis of plurisubstituted pyrroles
-
A versatile method for the synthesis of pyrroles is described using an intramolecular [3+2] cycloaddition reaction. This method allows the expedient preparation of 'plurisubstituted' compounds in which functionality is incorporated by choice, using appropriate readily available starting materials. Polycyclic pyrrole derivatives as well as 2-aryl monocyclic analogues are described. Several families of compounds are synthesized by sequential transformations. The method is designed to allow the creation of libraries with increased diversity of functionality by combinatorial or parallel synthesis.
- Bashiardes, George,Safir, Imad,Barbot, Francis,Laduranty, Joelle
-
p. 8417 - 8420
(2007/10/03)
-
- Microwave-Assisted [3 + 2] Cycloadditions of Azomethine Ylides
-
(Equation Presented) The microwave-assisted intramolecular [3 + 2] cycloaddition reaction of azomethine ylides to activated and nonactivated alkenes and alkynes is described. The procedure allows the synthesis of pyrrolidines and pyrrole products in good to excellent overall yields in short reaction times. It appears from parallel comparative studies that the microwave procedure favors the reaction times and overall purity of the crude reaction mixture. The reactions can also be performed in the absence of solvent.
- Bashiardes, George,Safir, Imad,Mohamed, Achmet Said,Barbot, Francis,Laduranty, Joelle
-
p. 4915 - 4918
(2007/10/03)
-
- Paradoxes in thermal stability of the liquid-crystal phase of phenylpropargyl phenyl ethers: I. Synthesis and mesogenic properties of phenylpropargyl phenyl ethers
-
The ethers PhC≡CCH2OC6H3RR′ were prepared in 51-83% yields by reactions of phenylpropargyl tosylate in alkaline solution with appropriate p- and o-substituted phenols. Below are given R, R′, and the ranges of existence of
- Shchelkunov,Abulyaisova,Mataeva,Sivolobova,Muldakhmetov
-
p. 1130 - 1132
(2007/10/03)
-
- Synthesis of novel bicyclic nitrogen heterocycles by the intramolecular dipolar cycloaddition reaction of nitrones with allenes and alkynes
-
A study of the intramolecular dipolar cycloaddition reactions of a series of allenyl and alkynyl nitrones has been carried out. Phenylhydroxylamine readily reacts with o-(1,2-propadienyloxy)benzaldehyde to give a dioxaazabicyclo[3.2.1]octene. The intramol
- Padwa, Albert,Meske, Michael,Ni, Zhijie
-
-
- 4? Participation of 1-Aza-1,3-butadienes in Cycloaddition Reactions: Intramolecular Diels-Alder Reactions of α,β-Unsaturated N-Sulfonylimines
-
The 4? participation of α,β-unsaturated N-sulfonylimines in intramolecular Diels-Alder reactions with unactivated dienophiles is detailed in studies which further extend the scope of the cycloaddition reactions of this new class of 1-aza-1,3-butadienes.Similar to observations made in the intermolecular cycloaddition reactions, a strong endo diastereoselectivity (>20:1) was observed to dominate in the cycloaddition reaction of 5b versus 5a and 5c.This endo specific reaction may be attributed to the combination of a pronounced, stabilizing secondary orbital interaction and preferred cycloaddition through an anti-endo transition state in which the lone pair on nitrogen and the C-aryl bond of the dienophile lie trans periplanar to one another benefiting from stabilization analogous to the ground-state anomeric effect.
- Boger, Dale L.,Corbett, Wendy L.
-
p. 2068 - 2074
(2007/10/02)
-