Fused ring aziridines as a facile entry into triazole fused tricyclic and bicyclic heterocycles.

نویسندگان

  • Fang Fang
  • Megan Vogel
  • Jennifer V Hines
  • Stephen C Bergmeier
چکیده

The intramolecular dipolar cycloaddition of an azide with an alkyne has provided a useful entry into triazole fused tricyclic heterocycles containing both the triazole ring and the oxazolidin-2-one ring system. The requisite azido-alkynes have been prepared via a two-step sequence from fused ring aziridines. A series of 6-12 membered rings containing both the oxazolidinone and triazole rings have been prepared. These ring systems have been designed as conformationally restrained analogs of RNA-binding oxazolidinones.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Photoreactions of bicyclic aziridines with alkenes and alkynes: a novel synthetic methodology for 8-azabicyclo[3.2.1]octane derivatives.

The photochemical C-C bond cleavage of bicyclic aziridines 7 and subsequent [3 + 2] cycloaddition with electron-deficient alkenes and alkynes afforded the novel head-to-head adducts selectively and efficiently. The adducts contain the naturally occurring 8-azabicyclo[3.2.1]octane skeleton (e.g. tropane alkaloids). The aziridine 8 fused with a 6-membered ring also afforded the cycloadducts but i...

متن کامل

Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions.

Syntheses of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined and discussed. The formation of (5,6)-membered systems was feasible with all nucleophiles tried (O, S and N), while the closing of the five-membered ring was restricted to O- and S-nucleophiles. The closure of a four-membered ring...

متن کامل

Rapid synthesis of medium-ring fused polycarbocyclic systems by rearrangement of carbenoid-derived oxonium ylides.

Tandem carbenoid generation, ylide formation and [2,3]-rearrangement is a powerful method for the construction of bicyclic and linearly fused tricyclic systems containing a seven-membered ring.

متن کامل

Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines.

A general and facile synthesis of enantiopure 1-deoxyazasugars was achieved from stereoselective dihydroxylation of a common synthetic intermediate, piperidine ring fused oxazolidin-2-one, originating from a commercially available starting substrate, chiral aziridine-2-carboxylate, in high yields.

متن کامل

Pyridoxine-derived bicyclic aminopyridinol antioxidants: synthesis and their antioxidant activities.

A few facile synthetic pathways for bicyclic aminopyridinol antioxidants are presented. Attachment of a long alkyl chain to the bicyclic pyridinol scaffold was established using ester linkage. Non-substituted pyrrolopyridinols and 1,3-oxazine-fused pyridinols were also synthesized as novel antioxidant scaffolds. Antioxidant activities were measured by a radical clock method and new compounds pr...

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 10 15  شماره 

صفحات  -

تاریخ انتشار 2012