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

Authors
Wang, Q Mikkola, S Lonnberg, H
Citation
Q. Wang et al., 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, TETRAHEDR L, 42(14), 2001, pp. 2735-2737
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
14
Year of publication
2001
Pages
2735 - 2737
Database
ISI
SICI code
0040-4039(20010402)42:14<2735:SO2TFE>2.0.ZU;2-2
Abstract
2,10,14, 18,22-Hexaazaspiro[11.11]tricosane 1 has been prepared in seven st eps from pentaerythritol. The key steps include two successive cyclizations by displacement of two tosyloxy groups from the appropriate pentaerythrito l derivatives (4: 6) with 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), each r eaction being followed by sodium borohydride reduction. Hydrolysis of the s piro bis(hexahydro-1 H,4H,7H-3a,6a,9a-triazaphenalene) formed 1. (C) 2001 E lsevier Science Ltd. All rights reserved.