Serendipitous synthesis of a cyclic formamidine. Application to the synthesis of polyazamacrocycles

被引：5

作者：

Simion, Cristian ^{[1
]}

Gherase, Dragos ^{[2
]}

Sima, Sergiu ^{[1
]}

Simion, Alina Marieta ^{[1
]}

机构：

[1] Univ Politehn Bucuresti, Fac Appl Chem & Mat Sci, Dept Organ Chem, Bucharest 060042, Romania

[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

COMPTES RENDUS CHIMIE | 2015年 / 18卷 / 06期

关键词：

Dimethylformamide; Hexahydro-1,3-diazonine; Formylation; Intramolecular condensation; Polyazamacrocycles; FORMYLATION; AMINES; MODELS;

D O I：

10.1016/j.crci.2014.12.006

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unexpected synthesis of 4,5,6,7,8,9-hexahydro-1,3-diazonine, using hexamethylenediamine and dimethylformamide, is presented. The cyclization process was explained as a two-step process involving formylation and subsequent intramolecular condensation. The scope of this process was demonstrated through the synthesis of two other nitrogen-containing macroheterocycles. (C) 2015 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

引用

页码：611 / 613

页数：3

共 18 条

[1] Formylation versus alkylation of secondary amines in DMF
Barrett, DMY
Kahwa, IA
Williams, DJ
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 2069 - 2071
[2] MODELS OF FOLATE COENZYMES .7. SYNTHESIS AND CARBON TRANSFER-REACTIONS OF N-5,N-10-METHENYL AND N-5,N-10-METHYLENETETRAHYDROFOLATE MODELS
BIERAUGEL, H
PLEMP, R
HIEMSTRA, HC
PANDIT, UK
[J]. TETRAHEDRON, 1983, 39 (23) : 3971 - 3979
[3] POLYMERS CONTAINING FORMAMIDINE GROUPS .5. FORMATION OF A CYCLIC FORMAMIDINE TRIMER BY THE CONDENSATION REACTION OF 2,6-DIAMINOPYRIDINE WITH TRIETHYL ORTHOFORMATE
BOHME, F
RILLICH, M
KOMBER, H
[J]. MACROMOLECULAR CHEMISTRY AND PHYSICS, 1995, 196 (10) : 3209 - 3216
[4] ALCOHOLS AND ALUMINUM ALKOXIDES IN THE PRESENCE OF RANEY-NICKEL AS ALKYLATING-AGENTS .3. REDUCTION OF SCHIFF-BASES WITH ISOPROPYL-ALCOHOL AND ALUMINUM ISOPROPOXIDE IN THE PRESENCE OF RANEY-NICKEL
BOTTA, M
DEANGELIS, F
GAMBACORTA, A
LABBIENTO, L
NICOLETTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) : 1916 - 1919
[5] Greber G., 1995, CHEM ABSTR, V123
[6] Janssen B., 1995, CHEM ABSTR, V123
[7] Binding of specialty phosphines to metals:: Synthesis, structure, and solution calorimetry of the phosphirane complex [PtMe2(iPrBABAR-Phos)2]
Laporte, C
Frison, G
Grützmacher, H
Hillier, AC
Sommer, W
Nolan, SP
[J]. ORGANOMETALLICS, 2003, 22 (11) : 2202 - 2208
[8] Phosphiranes as ligands for platinum catalysed hydrosilylations
Liedtke, J
Loss, S
Widauer, C
Grützmacher, H
[J]. TETRAHEDRON, 2000, 56 (01) : 143 - 156
[9] Liedtke J, 1999, ANGEW CHEM INT EDIT, V38, P1623, DOI 10.1002/(SICI)1521-3773(19990601)38:11<1623::AID-ANIE1623>3.0.CO
[10] 2-K

← 1 2 →