Synthesis of dihydroindeno[1,2-c]isochromene via cascade cyclization and Friedel–Crafts reaction

Saikia, Anil K.; Ghosh, Piyali; Deka, Manash Jyoti; Borah, Madhurjya

doi:10.1039/c6ra22329j

Cited by 5 publications

(2 citation statements)

References 36 publications

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“…In order to show the efficiency of the present method, we have compared our result obtained from the reaction of 4-chlorobenzaldehyde, resorcinol and malononitrile in the presence of (H-MOR/MIL-101-ED) with other results reported in the literature. [32][33][34][35] As can be seen in Table 3, this method avoids the disadvantages of other procedures, such as difficult work-up procedures, use of organic solvents, long reaction times and large amounts of catalysts.…”

Section: Study Of the Preparation Of Chromene Derivatives By Modifimentioning

confidence: 99%

Synthesis of chromene derivatives in the presence of mordenite zeolite/MIL‐101 (Cr) metal–organic framework composite as catalyst

Fallah

Sohrabnezhad

Abedini

2019

Applied Organom Chemis

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In the present study, the synthesis of mordenite zeolite/MIL‐101(Cr) metal–organic framework (MOF) composite [MOR/MIL‐101(Cr)] using the ship in a bottle method was suggested. The properties of prepared composite and individual MOF and MOR zeolite were characterized by X‐ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), nitrogen adsorption–desorption measurement, and thermogravimetric analysis (TGA). The XRD results indicated diffraction peaks for each compound (MOR and MOF) in composite. The SEM and TEM images showed the formation of plates MOR (with size of 2.5 × 3 μm) along with spherical particles MIL‐101. The Brunauer–Emmett–Teller results showed that the surface area of the composite was smaller than individual MOF and MOR zeolite. Based on TGA plots, the hybrid zeolite/MOF composite was more thermally stable compared with the isolated MIL‐101(Cr). The composite was functionalized by post‐synthetic modification to obtain acid–base bifunctionality (H‐MOR/MIL‐101‐ED) for the synthesis of chromene derivatives. The acidity from framework Al‐O(H)‐Si sites in MOR and basicity from amine groups in MIL‐101 were obtained by post‐synthetic modification.

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Section: Study Of the Preparation Of Chromene Derivatives By Modifimentioning

confidence: 99%

Synthesis of chromene derivatives in the presence of mordenite zeolite/MIL‐101 (Cr) metal–organic framework composite as catalyst

Fallah

Sohrabnezhad

Abedini

2019

Applied Organom Chemis

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“…For example, indenobenzofurans ( 1 ) could be accessed from (a) the acid-mediated condensation reactions of ninhydrins and polyphenols, ,,, and (b) the Hauser–Kraus annulation of phthalides and nitroalkenes (Figure ). On the other hand, indenoisochromenes ( 2 ) have been successfully synthesized from the alkynols and aromatic aldehydes via cascade cyclization/Friedel–Crafts reaction while the tricyclic 3 could be readily accessed from the arylvinyl epoxides and aldehydes/ketones via tandem Nazarov/oxa-Pictet–Spengler cyclization . The indenopyran ( 4 ) was prepared from the Prins cyclization of the corresponding homoallylic alcohol …”

Section: Introductionmentioning

confidence: 99%

Dihydro-10H-indeno[1,2-b]benzofurans and Tetrahydroindeno[1,2-c]isochromenes via Stereoselective Intramolecular Carbocation Cascade Cyclization

Tangdenpaisal,

Kheakwanwong,

Ruchirawat

et al. 2024

J. Org. Chem.

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Nazarov cyclization of the (E)-(2-stilbenyl)methanols under the catalysis of p-TsOH immobilized on silica (PTS-Si) proceeded to give the corresponding indanyl cation with the exclusive trans relationship at the two newly formed adjacent stereogenic centers. The ensuing intramolecular nucleophilic addition by the MOM-protected phenol (m = 0) or benzyl alcohol (m = 1) furnished the Indane-fused benzofuran [5/5] or isochroman [5/6] system, respectively, with the exclusive cis stereocontrol at the two-carbon ring junction. Thus, in a single step, from nonchiral starting materials, the intramolecular cascade carbocation cyclization (CCC) furnished the [5/5] or [5/6] oxygen-containing Indane fused-ring systems in moderate to good yields with excellent stereoselectivity on all three contiguous stereogenic centers.

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The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations

et al. 2021

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Synthesis of dihydroindeno[1,2-c]isochromene via cascade cyclization and Friedel–Crafts reaction

Abstract: Dihydroindeno[1,2-c]isochromene can be efficiently prepared from alkynol and aldehydes via cascade cyclization and Friedel–Crafts reaction. The reaction is highly regioselective.

Cited by 5 publications

References 36 publications

Synthesis of chromene derivatives in the presence of mordenite zeolite/MIL‐101 (Cr) metal–organic framework composite as catalyst

Synthesis of chromene derivatives in the presence of mordenite zeolite/MIL‐101 (Cr) metal–organic framework composite as catalyst

Dihydro-10H-indeno[1,2-b]benzofurans and Tetrahydroindeno[1,2-c]isochromenes via Stereoselective Intramolecular Carbocation Cascade Cyclization

The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations

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