Synthesis of 2,6,10,14,18,22-hexaazaspiro[11.11]tricosane, the first example of a spiro aza crown derived from 2,2-bis(aminomethyl)propane-1,3-diamine



: Wang Q, Mikkola S, Lonnberg H

Publisher: PERGAMON-ELSEVIER SCIENCE LTD

: 2001

: Tetrahedron Letters

: TETRAHEDRON LETTERS

: TETRAHEDRON LETT

: 42

: 14

: 2735

: 2737

: 3

: 0040-4039

DOI: https://doi.org/10.1016/S0040-4039(01)00238-6


2,10,14, 18,22-Hexaazaspiro[11.11]tricosane 1 has been prepared in seven steps from pentaerythritol. The key steps include two successive cyclizations by displacement of two tosyloxy groups from the appropriate pentaerythritol derivatives (4: 6) with 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), each reaction being followed by sodium borohydride reduction. Hydrolysis of the spiro bis(hexahydro-1 H,4H,7H-3a,6a,9a-triazaphenalene) formed 1. (C) 2001 Elsevier Science Ltd. All rights reserved.



Last updated on 2024-26-11 at 16:07