Stepwise π-extension of meso-alkylidenyl porphyrins through sequential 1,3-dipolar cycloaddition and redox reactions.
نویسندگان
چکیده
Several regioselectively π-extended, pyrrole fused porphyrinoids have been synthesized by the 1,3-dipolar cycloaddition of meso-alkylidene-(benzi)porphyrins. Pd(II) complexes gave oxidation resistant, bis-pyrrole fused adducts. The repeated 1,3-dipolar cycloaddition followed by oxidation-reduction of pentaphyrin analogs afforded π-extended porphyrin analogs.
منابع مشابه
A 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 competitive Diels-Alder/1, 3-dipolar cycloaddition reaction of1-H-imidazole 3-oxide toward sulfonyl methane. A DFT study on the energetic and regioselectivity
The dual diene/1,3-dipolar character of 1-H-imidazole 3-oxide, HIO 1, allows this compound toparticipate in a competitive Diels-Alder (DA)/1,3-dipolar cycloaddition (13DC) reaction toward C=Sdouble bond of the electro-deficient sulfonyl methane SFM 2. The B3LYP/6-311++G(d,p) calculatedrelative Gibbs free energies indicate that among the studied 13DC and DA reactions, former iscompletely preferr...
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 کاملImpact of Lewis acid catalyst on the regioselectivity and kinetics of 1,3-dipolar cycloaddition reaction of azidobenzene with acrolein: a theoretical study using DFT
In the present work, impact of Lewis acid (LA) catalysts BF3, BCl3, and BBr3 on the kinetics andregioselectivity of 1,3-dipolar cycloaddition (1,3-DC) reaction between azidobenzene and acroleinwas theoretically studied using B3LYP/6-31G* level. Our results indicate while the uncatalyzed 1,3-DC reaction under investigation takes place via a non-polar, non-regioselective, and lowasynchronous proc...
متن کاملA Novel Strategy of Ugi-4CR/Huisgen 1,3-Dipolar Synthesis of 1H-1,2,3-Triazole-Modified Peptidoimetics
In this protocol, we report a novel approach for the synthesis of a new class of heterocyclic 1H-1,2,3-triazole-modified peptidomimetic compounds. The process consists of an Ugi four-component condensation reaction of amines, an isocyanide, an aldehyde and acids followed by a Huisgen 1,3-dipolar cycloaddition reaction with an azide group in the presence of a catalytic amount of CuSO4</...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical communications
دوره 50 66 شماره
صفحات -
تاریخ انتشار 2014