New  Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton

Tanase, Constantin I.; Draghici, Constantin; Negut, Catalina; Pintilie, Lucia

Constantin I. Tanase, Constantin Draghici, Catalina Negut, Lucia Pintilie

New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton

Abstract:

In this paper we present an efficient procedure for obtaining ether-protected bicyclo[2.2.1]heptane amines in six steps, from an optically active keto-alcohol norbornane compound, for building the heterocyclic bases of pyrimidine and purine constrained nucleosides. Trityl as protecting group makes it possible to isolate 5-endo-compounds in pure form by selective crystallization, and to isolate the intermediates in the next 3 steps of the reaction by crystallization. With TBDMS, all compounds were obtained as oil. The direct selective reduction of the keto-alcohol norbornane compound gave the pure 5-endo-diol 4d in high yield, which was then selectively protected at the primary hydroxyl with a trityl group; the next steps are similar for obtaining the trityl-protected bicyclo[2.2.1]heptane amine. The azide intermediates are valuable intermediates for click chemistry.

Keywords:
selective NaBH4 reduction; bicyclo<2.2.1>heptane amines; bicyclo<2.2.1>heptane azides; mesyl substitution; azide reduction

Issue: 2018, Volume 69, Issue 9

Pages: 2448-2453

Publication date: 2018/10/15

https://doi.org/10.37358/RC.18.9.6551

Download Pdf Article

This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
TANASE, C.I., DRAGHICI, C., NEGUT, C., PINTILIE, L., New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton, Rev. Chim., 69(9), 2018, 2448-2453.

Vancouver
Tanase CI, Draghici C, Negut C, Pintilie L. New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton. Rev. Chim.[internet]. 2018 Sep;69(9):2448-2453. Available from: https://doi.org/10.37358/RC.18.9.6551

APA 6th edition
Tanase, C.I., Draghici, C., Negut, C. & Pintilie, L. (2018). New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton. Revista de Chimie, 69(9), 2448-2453. https://doi.org/10.37358/RC.18.9.6551

Harvard
Tanase, C.I., Draghici, C., Negut, C., Pintilie, L. (2018). 'New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton', Revista de Chimie, 69(9), pp. 2448-2453. https://doi.org/10.37358/RC.18.9.6551

IEEE
C.I. Tanase, C. Draghici, C. Negut, L. Pintilie, "New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton". Revista de Chimie, vol. 69, no. 9, pp. 2448-2453, 2018. [online]. https://doi.org/10.37358/RC.18.9.6551

Text
Constantin I. Tanase, Constantin Draghici, Catalina Negut, Lucia Pintilie,
New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton,
Revista de Chimie,
Volume 69, Issue 9,
2018,
Pages 2448-2453,
ISSN 2668-8212,
https://doi.org/10.37358/RC.18.9.6551.
(https://revistadechimie.ro/Articles.asp?ID=6551)
Keywords: selective NaBH4 reduction; bicyclo<2.2.1>heptane amines; bicyclo<2.2.1>heptane azides; mesyl substitution; azide reduction

RIS
TY - JOUR
T1 - New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton
A1 - Tanase, Constantin I.
A2 - Draghici, Constantin
A3 - Negut, Catalina
A4 - Pintilie, Lucia
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2018
VL - 69
IS - 9
SP - 2448
EP - 2453
UR - https://doi.org/10.37358/RC.18.9.6551
KW - selective NaBH4 reduction; bicyclo<2.2.1>heptane amines; bicyclo<2.2.1>heptane azides; mesyl substitution; azide reduction
ER -

BibTex
@article{RevCh2018P2448,
author = {Tanase Constantin I. and Draghici Constantin and Negut Catalina and Pintilie Lucia},
title = {New Constrained Amines in a Bicyclo<2.2.1>Heptane Skeleton},
journal = {Revista de Chimie},
volume = {69},
number = {9},
pages = {2448-2453},
year = {2018},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.18.9.6551},
url = {https://revistadechimie.ro/Articles.asp?ID=6551}
}

<<<< back

PUBLISHING SECTION

Author Guidelines

* Paper Drafting

* Paper Template

* Ethical Statement

* Paper Submission

Ghidul Autorului (ro)

Open Access & Archiving Policy

Search Authors

LATEST NEWS
	NUMAR OMAGIAL PETRU PONI.. detalii
	Revista de Chimie - 70 de ani de aparitie neintrerupta.. detalii
	English-Romanian Dictionary for Mechanical Engineering (download pdf)