Direct Lactamization of Azido Amides via Staudinger-Type Reductive Cyclization

Heo, In-Jung; Lee, Su-Jeong; Cho, Chang-Woo

doi:10.5012/bkcs.2012.33.1.333

Cited by 8 publications

(5 citation statements)

References 26 publications

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“…A dehydrogenative ring closure of an α,ω-aminoalcohol, catalyzed by a pincer-ligated divalent iron complex, was reported to yield 49% of the product (Scheme , eq 2) . Much higher yields were obtained , when an acyclic azide was converted into morpholin-3-one in Bu 3 SnH- or Ph 3 P-mediated processes (Scheme , eq 3), but in both cases, formation of stoichiometric byproducts makes the synthesis relatively unattractive, especially on a large scale. In the only scaled example of the target compound preparation a high-temperature reaction between dioxanone and a large excess of ammonia was used (Scheme , eq 4).…”

Section: Building Blocksmentioning

confidence: 99%

Review on Synthetic Approaches toward Rivaroxaban (Xarelto), an Anticoagulant Drug

Mladentsev

Kuznetsova

Skvortsova

et al. 2022

Org. Process Res. Dev.

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Venous thromboembolism including deep vein thrombosis and pulmonary embolism is an abundant and dangerous disease with significant relapse probability and mortality. In pursuit of an effective treatment, Bayer created Rivaroxaban, nowadays known under the brand name Xarelto, that was approved by the FDA in 2011. By 2022, the number of main indications for the drug has been increased 10-fold as well as the drug's prevalence in the field of thrombosis treatment. It is therefore apparent that with growing prescriptions new synthetic pathways are highly desirable, especially those utilizing inexpensive and safe reagents in environmentally benign protocols. The present work reviews the literature concerning Rivaroxaban preparation with an emphasis on the applicability of synthetic pathways on a large scale. Within the synthetic sequences, common intermediates are discussed in detail and relevant comparisons are made. Our main purpose is to provide an overview of the subject in its current state, paying attention to advances made and suggesting possible directions for further development.

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Section: Building Blocksmentioning

confidence: 99%

Review on Synthetic Approaches toward Rivaroxaban (Xarelto), an Anticoagulant Drug

Mladentsev

Kuznetsova

Skvortsova

et al. 2022

Org. Process Res. Dev.

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“…This method gives access to 3,4-dihydroisoquinolin-1(2H)-one 1 by direct lactamization of azido amide 36 under mild reaction conditions. [31] Additionally, the same research group also developed the procedure for the cyclization of azidoamide 36 to 3,4dihydroisoquinolin-1(2H)-one 1 in presence of the tributyltin hydride. This procedure produces 3,4-dihydroisoquinolin-1(2H)one 1 in 92% yield (Scheme 10).…”

Section: Intramolecular Cyclization Of Carbamate/ Urea/ Thiourea/ Isomentioning

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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“…Traditional approaches to access 3,4-dihydroisoquinolones mainly rely on intramolecular cyclization of activated amide or amide precursors, including carbamates, − isocynates, , ureas, and azidoamides. , However, most of these methods suffer from limited substrate scope resulting from the use of strongly acidic conditions. Recently, significant effort has been devoted to the preparation of 3,4-dihydroisoquinolones, with representative methods including (1) palladium catalyzed carbonyl insertion (Scheme a); − (2) oxidation of cyclic amines (Scheme b); − and (3) [4 + 2] cycloaddition of activated arylamides with alkenes via transition-metal-catalyzed C–H activation (Scheme c). − Despite substantial progress, most of these methods still leave room for improvement to address the use of prefunctionalized substrates, expensive metal catalysts and ligands, the need for excess oxidants, or tedious procedures.…”

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confidence: 99%

“…13 Consequently, the development of efficient methods for the synthesis of this important N-heterocycle core has attracted much attention.Traditional approaches to access 3,4-dihydroisoquinolones mainly rely on intramolecular cyclization of activated amide or amide precursors, including carbamates, 14−16 isocynates, 17,18 ureas, 19 and azidoamides. 20,21 However, most of these methods suffer from limited substrate scope resulting from the use of strongly acidic conditions. Recently, significant effort has been devoted to the preparation of 3,4-dihydroisoquinolones, with representative methods including (1) palladium catalyzed carbonyl insertion (Scheme 2a); 22−24 (2) oxidation of cyclic amines (Scheme 2b); 25−27 and (3) [4 + 2] cycloaddition of activated arylamides with alkenes via transition-metal-catalyzed C−H activation (Scheme 2c).…”

mentioning

confidence: 99%

Base-Promoted Tandem Synthesis of 3,4-Dihydroisoquinolones

Wang

Jin

et al. 2022

Org. Lett.

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Using benzaldehydes, NaN(SiMe3)2, and N-acylpyrroles, an operationally simple tandem method to produce a wide array of 3,4-dihydroisoquinolones is presented (37 examples, yields up to 98%). A unique feature of this method stems from the sequential aminobenzylation of aldehydes and transamidation of the corresponding N-(trimethylsilyl)imines in one pot. In this process, three new bonds are generated (one C–C and two C–N bonds).

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Direct Lactamization of Azido Amides via Staudinger-Type Reductive Cyclization

Cited by 8 publications

References 26 publications

Review on Synthetic Approaches toward Rivaroxaban (Xarelto), an Anticoagulant Drug

Review on Synthetic Approaches toward Rivaroxaban (Xarelto), an Anticoagulant Drug

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

Base-Promoted Tandem Synthesis of 3,4-Dihydroisoquinolones

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