Dimroth Rearrangement

doi:10.1002/9780470638859.conrr194

Comprehensive Organic Name Reactions and Reagents 2010

DOI: 10.1002/9780470638859.conrr194

|View full text |Cite

Dimroth Rearrangement

Abstract: The base‐catalyzed rearrangement or translocation of exo ‐ and endo ‐cyclic heteroatoms on a heterocyclic ring is generally referred to as the Dimroth rearrangement. This type of rearrangement has been reported to occur on a six‐membered ring but is also possible for five‐membered rings. Many Dimroth rearrangements involve 1H‐1,2,3‐triazoles.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2020

2022

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Renaissance of Ring‐Opening Chemistry of Benzotriazoles: New Wine in an Old Bottle

Wang

Tang

2020

The Chemical Record

View full text Add to dashboard Cite

Abstract1,2,3‐Benzotriazoles could undergo ring cleavage to form ortho‐amino arenediazonium or α‐diazo‐imine species via a Dimroth‐type equilibrium. Historically, the synthetic potential of this unique reactivity had remained underdeveloped. Recently, some new strategies have been developed to effect the ring‐opening chemistry of benzotriazoles in more practical manners. A wide range of conceptually novel and synthetically useful reactions have been developed, which enable the access to diverse valuable heterocycles and ortho‐amino arene derivatives. As one of the players in this field, our group has also contributed a series of intriguing transition‐metal‐catalyzed denitrogenative functionalizations of benzotriazoles. In this account, we aim to provide an overview of the ring‐opening chemistry of benzotriazoles, with a focus on relevant works published in the past decade. In order to show a whole picture of the research field, some pioneering works in its developing history will also be discussed briefly.

show abstract

Renaissance of Ring‐Opening Chemistry of Benzotriazoles: New Wine in an Old Bottle

Wang

Tang

2020

The Chemical Record

View full text Add to dashboard Cite

show abstract

Metal-Free [5 + 1] Cycloaddition–Aromatization of Benzotriazoles and Sulfur Ylides to Construct 1,2,4-Benzotriazines

Wang

Mao

et al. 2022

Org. Lett.

View full text Add to dashboard Cite

Reported herein is a novel [5 + 1] cycloaddition− aromatization of benzotriazoles and sulfur ylides to efficiently construct 1,2,4-benzotriazine derivates with good yield. This new protocol does not employ any transition metal reagent and enables the cycloaddition by cleavage of the N−N single bond. The use of inexpensive and readily available starting materials, a broad substrate scope, mild reaction conditions, metal-free, and versatile functionalization of the 1,2,4-benzotriazines make this strategy more attractive.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Dimroth Rearrangement

Cited by 2 publications

References 64 publications

Renaissance of Ring‐Opening Chemistry of Benzotriazoles: New Wine in an Old Bottle

Renaissance of Ring‐Opening Chemistry of Benzotriazoles: New Wine in an Old Bottle

Metal-Free [5 + 1] Cycloaddition–Aromatization of Benzotriazoles and Sulfur Ylides to Construct 1,2,4-Benzotriazines

Contact Info

Product

Resources

About