C–H functionalization enabled stereoselective Ugi-azide reaction to α-tetrazolyl alicyclic amines

Haldar, Surajit; Saha, Subhajit; Mandal, Sumana; Jana, Chandan K.

doi:10.1039/c8gc01544a

Cited by 23 publications

(7 citation statements)

References 63 publications

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“…for the first time reported the azido‐Ugi reaction of THIQs 20 , isocyanides 21 , 9‐fluorenone 30 and TMS‐azide 31 in methanol at 90 °C (Scheme 5). [23] A wide range of C1‐tetrazolyl THIQs 35 was obtained in moderate to excellent yields (64–96%). This process begins with formation of iminium intermediates 32 via condensation of THIQs 20 and 9‐fluorenone 30 .…”

Section: C1‐functionalizationmentioning

confidence: 98%

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs)

et al. 2021

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1,2,3,4‐tetrahydroisoquinoline (THIQ) and its derivatives possess a widespread biochemical, pharmaceutical and biological properties and they are the key building blocks in the structure of drugs and natural alkaloids. Accordingly, construction of multi‐substituted and polycyclic THIQs through functionalization of THIQs at different positions especially at C1‐position have come to the center of attraction in recent studies. In this review, we've focused on the classification of C1‐functionalization of THIQs in the research articles from 2013 on, including a brief description of the reaction mechanisms for the synthesis of multi‐substituted and polycyclic THIQs based on the type of substituents at the 1‐position of the THIQ moiety. From this point of view, the main categories are C1‐Functionalization and C1‐Functionalization with annulation.

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Section: C1‐functionalizationmentioning

confidence: 98%

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs)

et al. 2021

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“…Jana and coworkers developed a redox-Ugi-azide fourcomponent reaction (Scheme 53). 100 These reactions involve trapping of the nitrilium ion intermediates by TMSN3, generating α-tetrazolyl amines (e.g., 107).…”

Section: Redox-ugi Reactionsmentioning

confidence: 99%

Condensation-Based Methods for the C–H Bond Functionalization of Amines

Chen

Seidel

2021

Synthesis

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This review aims to provide a comprehensive overview of condensation-based methods for the C–H bond functionalization of amines that feature azomethine ylides as key intermediates. These transformations are typically redox-neutral and share common attributes with classic name reactions such as the Strecker, Mannich, Friedel−Crafts, Pictet−Spengler, and Kabachnik−Fields reaction, while incorporating a redox-isomerization step. This approach provides an ideal platform to rapidly transform simple starting materials into complex amines.

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“…The absolute configurations of products were determined from crystallographic studies. Lindermann 29 and his co-workers developed a convertible isonitrile and applied in asymmetric Ugi reaction in 1999. Both aliphatic and aromatic aldehydes can be tolerated in this reaction leading to optically pure amino acids with noteworthy diastereoselectivity (Scheme 38).…”

Section: Scheme 37mentioning

confidence: 99%

A concise review on the stereoselective synthesis of chiral α-bisamides using stereoselective Ugi-type reaction

Ramakrishna¹,

Pradhan²

2021

Arkivoc

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To ensure a sustainable development, the "twelve principles of green chemistry" have been proposed for the field of synthetic organic chemistry. The stereoselective Ugi reaction is one of the most widely used reactions with high atom economy to prepare chiral α-bisamides and this reaction satisfies many of the green chemistry principles. The recent achievements in this reaction include one pot synthetic methodology, aqueous phase transformations and solvent free transformations even at ambient conditions. This review summarizes the progress recorded in this field over the past 20 years.Retrosynthetic methodology for the synthesis of Chiral α-bisamide

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C–H functionalization enabled stereoselective Ugi-azide reaction to α-tetrazolyl alicyclic amines

Abstract: An unprecedented stereoselective C–H functionalization enabled Ugi-azide (CH-Ugi-azide) reaction to access α-tetrazolyl alicyclic amines directly from N-heterocycles is reported.

Cited by 23 publications

References 63 publications

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs)

C1‐Functionalization of 1,2,3,4‐Tetrahydroisoquinolines (THIQs)

Condensation-Based Methods for the C–H Bond Functionalization of Amines

A concise review on the stereoselective synthesis of chiral α-bisamides using stereoselective Ugi-type reaction

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