DBU-Promoted Cyclization of ortho-(3-Hydroxy-1-alkynyl)benzamide: Synthesis of trans-3,4-Dihydroisoquinolin-1(2H)-ones and (E)-4-(1-Alkenyl)isoquinolin-1(2H)-ones

Chen, Wanli; Cui, Jing; Zhu, Yuelin; Hu, Xian-Chao; Mo, Weimin

doi:10.1021/jo2022907

Cited by 25 publications

(6 citation statements)

References 37 publications

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“…By this method trans-3,4-dihydroisoquinolin-1(2H)ones and (E)-4-(1-alkenyl)isoquinolin-1(2H)-ones synthesized in good to moderate yields with a variety of substituents on aliphatic ring (Scheme 66 and 67). [84] Ji-Bao Xia et al synthesized the chiral isoquinolinone by palladium catalyzed enantioselective C-H aminocarbonylation The synthesized chiral isoquinolinone (180) transferred to the useful compounds without the loss of the chiral purity (Scheme 68). [85] Jianguo Yang et al synthesized the chiral 3,4-dihydroisoquinolin-1(2H)-one by asymmetric palladium catalyzed C-H functionalization by cascade approach.…”

Section: Scheme 42 Synthesis 4-hydroxyalkyl-substituted 34-dihydroimentioning

confidence: 99%

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Kulkarni

Gaikwad

2020

ChemistrySelect

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The 3,4‐dihydroisoquinolin‐1(2H)‐one motifs found in many natural products, synthetic molecules with a diverse range of the biological activities and represent a privilege scaffold. Thereby the number of the innovative synthetic methodologies has been reported for constructions of this scaffold, which includes metal catalyzed and metal free method, multicomponent, domino one pot protocol, oxidation, Friedel‐Crafts type of cyclization. In the recent years many general protocols for the construction of this scaffold were reported in the literature and there is no focussed individual review for the 3,4‐dihydroisoquinolin‐1(2H)‐one since 2001. This review focuses on the reports describing the new method for the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐one, published since 2001 to till date. In this review, we approach method of the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐one according to the strategy used for its synthesis, which includes, the intramolecular cyclization of carbamate/ urea/ thiourea/ isocyanate/ azidoamide, carbonylation/ carbomylation/ carbonyl insertion, metal catalyzed protocols by C−H activation by directing group, metal free domino procedures and oxidations of isoquinoline derivatives that were included in recent publications. Moreover, the reports published since 2001 for the synthesis of the chiral 3,4‐dihydroisoquinolin‐1(2H)‐one are included.

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Section: Scheme 42 Synthesis 4-hydroxyalkyl-substituted 34-dihydroimentioning

confidence: 99%

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Kulkarni

Gaikwad

2020

ChemistrySelect

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“…1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU), a kind of organic amine, was developed in 1960s and has been investigated for many years. It is a useful catalyst for many reactions, such as elimination reaction, condensation, migration of double bond, cyclization, and active methylene reaction . As the organic synthesis developed, DBU has been attracted more and more attention by many chemists.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Four‐component Reaction for the Synthesis of Spiroheterocyclic Compounds

Meng

et al. 2016

Journal of Heterocyclic Chem

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A series of 6‐amino‐8‐aryl‐3,4‐dihydro‐1H‐spiro[naphthalene‐2,2'‐[1,3] dioxolane]‐5,7‐dicarbonitrile and 8‐arylidene‐4‐aryl‐7,8‐dihydro‐5H‐spiro[quinazoline‐6,2'‐[1,3] dioxolan]‐2‐amine derivatives have been synthesized from the reactions of 1,4‐dioxaspiro[4.5] decan‐8‐one, aromatic aldehydes, and malononitrile (or guanidine carbonate) under different conditions with high yields. In this research, it was found the DBU–THF was efficient reaction condition for obtaining 6‐amino‐8‐aryl‐3,4‐dihydro‐1H‐spiro[naphthalene‐2,2'‐[1,3]dioxolane]‐5,7‐dicarbonitrile derivatives, while 95% EtOH and NaOH was the preferred condition for the synthesis of 8‐rylidene‐4‐aryl‐7,8‐dihydro‐5H‐spiro[quinazoline‐6,2'‐[1,3]dioxolan]‐2‐amine derivatives. To the best of our knowledge, these Spiroheterocycles were first reported in our research. The other advantages of this process were short‐reaction time, wide scope substrates, and simple set‐up.

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“…reported the synthesis of α-amidoketones from alkynylated amides obtained by direct alkylation using NaH . Cyclic α-amidoketones can be generated by DPU-promoted cyclization of alkynyl-substituted benzamides . Recently, Yamamoto and co-workers described the synthesis of α-amidoketones starting from methyleneaziridines.…”

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confidence: 99%

Synthesis of α-Amidoketones from Vinyl Esters via a Catalytic/Thermal Cascade Reaction

2016

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A straightforward, modular, and atom-efficient method is reported for the synthesis of α-amidoketones from vinyl esters via a cascade reaction including hydroformylation, condensation with a primary amine, and a rearrangement step giving water as the only byproduct. The reaction sequence can be performed in one pot or as a three-step procedure. The synthetic applicability is demonstrated by the preparation of different α-amidoketones in moderate to good yields.

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DBU-Promoted Cyclization of ortho-(3-Hydroxy-1-alkynyl)benzamide: Synthesis of trans-3,4-Dihydroisoquinolin-1(2H)-ones and (E)-4-(1-Alkenyl)isoquinolin-1(2H)-ones

Abstract: DBU-promoted cyclization of ortho-(3-hydroxy-1-alkynyl)benzamide is presented, providing an efficient method for the synthesis of trans-3,4-dihydroisoquinolin-1(2H)-ones and (E)-4-(1-alkenyl)isoquinolin-1(2H)-ones under mild conditions.

Cited by 25 publications

References 37 publications

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

An Efficient Four‐component Reaction for the Synthesis of Spiroheterocyclic Compounds

Synthesis of α-Amidoketones from Vinyl Esters via a Catalytic/Thermal Cascade Reaction

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