Unprecedented synthesis of aza-bridged benzodioxepine derivatives through a tandem Rh(II)-catalyzed 1,3-rearrangement/[3+2] cycloaddition of carbonyltriazoles.
نویسندگان
چکیده
Rh(II)-catalyzed novel tandem intramolecular cycloisomerizations of aldehydes or ketones with 1-sulfonyl 1,2,3-triazoles have been disclosed, providing a facile protocol to access a series of functionalized aza-bridged benzodioxepine heterocycles.
منابع مشابه
Rh(II)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon.
The Rh(II)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions.
متن کاملSynthesis of [RhCl(CO)(cyclopentadienone)]2 from [RhCl(cod)]2 and a 1,6-diyne under CO: application to Rh(I)-catalyzed tandem [2+2+1] carbonylative cycloaddition of diynes and Claisen rearrangement.
Although Rh(I)Cl(CO)(cpd) (cpd = cyclopentadienone) complexes were identified more than 40 years ago, their exact structures have not been determined because of the polymeric nature of these complexes. We determined the structure of [Rh(I)Cl(CO)(cpd)](2), which was formed by the reaction of [Rh(cod)Cl](2) with a 1,6-diyne under CO. In addition, based on determination of the structure of the [Rh...
متن کاملRhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkynew
The Diels–Alder cycloaddition is arguably the most powerful reaction for the construction of substituted six-membered rings from various 2p and 4p reactants. However, unactivated 2p and 4p systems either require very harsh conditions or fail to undergo cycloadditions. In many cases, transition metal catalysts facilitated chemical transformations that were inaccessible under thermal conditions a...
متن کاملA Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives
The development of multicomponent reactions (MCRs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. A comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarc...
متن کاملA Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives
The development of multicomponent reactions (MCRs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. A comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarc...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 50 100 شماره
صفحات -
تاریخ انتشار 2014