Advanced search
Publication Cover
Phosphorus, Sulfur, and Silicon and the Related Elements Volume 126, 1997 - Issue 1
Submit an article Journal homepage
54
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

N-PHOSPHORYLATED NITROGEN MUSTARDS; PREPARATION OF 2-CHLOROETHYL- AND BIS(2-CHLOROETHYL)-AMIDES WITH THE BENZODIAZAPHOSPHORINONE RING SYSTEM

Ralf Sonnenburg Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329, D-38023, Braunschweig, Germany
,
Frank Borkenhagen Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329, D-38023, Braunschweig, Germany
,
Ion Neda Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329, D-38023, Braunschweig, Germany
,
Holger Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329, D-38023, Braunschweig, Germany
,
Thönnessen Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329, D-38023, Braunschweig, Germany
,
Peter G. Jones Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329, D-38023, Braunschweig, Germany
&
Reinhard Schmutzler Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329, D-38023, Braunschweig, Germany; R. Schmutzler, Institut für Anorganische und Analytische Chemie der Technischen Universität, Postfach 3329, D-38023, Braunschweig, Germany
 show all
Pages 11-26 | Received 26 Nov 1996, Published online: 04 Oct 2006
 
Sample our Physical Sciences journals, sign in here to start your FREE access for 14 days

Abstract

The reaction of isatoic acid anhydride 1 with NaH/BrCH2CH2Cl furnished the N-(2-chloroethyl) substituted derivative 2, which was allowed to react with methylamine to form N-(2-chloroethyl)-N′ methylanthranilamide 3, Treatment of 3 with PCI3 furnished the 1,3,2-diazaphosphorin-4-one 4, which reacted with bis(2-chloroethyl) amine hydrochloride to form the P-bis(2-chloroethyl) amino derivative 5 by substitution at phosphorus. Oxidation of 5 with the hydrogen peroxide/urea 1:l adduct led to the phosphoryl species 6, Theσ4P-derivative 7 was formed by hydrolysis of 4 with small amounts of water. Treatment of the P-chloro derivative 8 with (CH3)3SiOCH3 furnished the methoxy-substituted compound 9, which formed the phosphoryl derivative 10 upon reaction with SO2Cl2. The previously known bis(2-chloroethyl)amino-substituted 1,3,2-benzodiazaphosphorin-4-on-2-oxide 11 was synthesized by reaction of 10 with bis(2-chloroethyl) amine hydrochloride/triethylamine. The P-2-chloroethylamino-substituted derivative 12 was obtained by treatment of 8 with 2-chloroethylarnine hydrochloride/triethylamine. The structures of 3, 4 and 5 were confirmed by single crystal X-ray structure determination. In 3 the molecules are linked into chains by hydrogen bonds of the form N-H···O=C between amide groups. The heterocycles of 4 and 5 display half-boat conformation with the P atom out of plane.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related Research Data

Studies on the Synthesis of Phosphorus Heterocyles II. Preparation of Some New Tetrahydro-[1,4,3]thiazaphosphorino[3,4-b][1,3,2]benzodiazaphosphorine 12-Oxides
Source: Georg Thieme Verlag KG
Studies on the Synthesis of Phosphorus Heterocycles I. [1,4,3]Thiazaphosphorino[3,4-b][1,3,2]benzodiazaphosphorine 12-Oxides
Source: Georg Thieme Verlag KG
THE CHEMISTRY OF 2H‐3,1‐BENZOXAZINE‐2,4(1H)DIONE (ISATOIC ANHYDRIDES) PART 1, THE SYNTHESIS OF N‐SUBSTITUTED 2H‐3,1‐BENZOXAZINE‐2,4(1H)DIONES
Source: Wiley
VERBINDUNGEN MIT DEM 1,3,2-BENZODIAZAPHOSPHORINAN-4-ON GRUNDGERÜST: SYNTHESE VON NEUARTIGEN, N,N-DIMETHYLAMINO- UND BIS-2-CHLORETHYLAMINO-SUBSTITUIERTEN DERIVATEN MIT DREI-, VIER- UND FÜNFFACH KOORDINIERTEM PHOSPHOR
Source: Informa UK Limited
Novel heterocycles. 3. Synthesis of fused 1,3,2-benzodiazaphosphorin ring systems
Source: Wiley
PREPARATION OF N-PHOSPHORYLATED NITROGEN MUSTARDS WITH THE BENZODIAZA- AND OXAZAPHOSPHORINONE RING SYSTEMS;HYDROLYSIS OF 2-CHLORO BENZODIAZAPHOSPHORINONES
Source: Informa UK Limited
Umsetzung einiger Dihydrobenzoxazaphosphorinone mit Nucleophilen; ungewöhnliche Oxidations‐, Insertions‐ und Umlagerungsprodukte und deren Charakterisierung durch Einkristall‐Röntgenstrukturanalyse
Source: Wiley
DARSTELLUNG UND CHARAKTERISIERUNG VON 2-AMINO- UND 2-METHOXYSUBSTITUIERTEN BENZODIAZAPHOSPHORINONEN MIT PHOSPHOR IN DEN KOORDINATIONSZAHLEN DREI, VIER UND FÜNF
Source: Informa UK Limited
Synthesis of Tricyclic (λ5)‐Phosphoranes; unusual N‐demethylation/N‐alkylation reactions during the oxidative addition of hexafluoroacetone and tetrachloro‐ortho‐benzoquinone to benzodiaza‐λ3‐phosphorinones. Single crystal X‐ray diffraction studies of various products
Source: Wiley
CCDC 104188: Experimental Crystal Structure Determination
Source: Cambridge Crystallographic Data Centre
CCDC 104187: Experimental Crystal Structure Determination
Source: Cambridge Crystallographic Data Centre
Crystal structure of 1,3-di-tert-butyl-2-chloro-1,3,2-di-aza-phospho-rinane - a saturated six-membered phospho-rus nitro-gen heterocycle with a partially flattened chair conformation and a long PIII-Cl bond.
Source: International Union of Crystallography
Umsetzungen von 0,3-Dialkyl-1,3-diaza-2-chloro-5,6-benzo-1,3,2-phosphorinan-4-onen; Darstellung von P(III)-Derivaten / Reactions of 1,3-Dialkyl-1,3-diaza-2-chloro-5,6-benzo-1,3,2-phosphorinan-4-ones; Preparation of P(III) Derivatives
Source: Walter de Gruyter GmbH
Verbindungen mit dem 5,6-Benzo-l,3,2-diazaphosphorinan-4-on-Ringsystem: Synthese von 2-Chlor-, 2-N,N-dimethylamino-und 2-Bis-(2-chlorethyl)amino- substituierten Derivaten mit drei-und vierfach koordiniertem Phosphor / Compounds Involving the 5,6-Benzo-l,3,2-diazaphosphorinane-4-one Ring System: Synthesis of 2-Chloro-, 2-N,N-dimethylamino-and 2-Bis-(2-chloroethyl)amino- Substituted Derivatives with Three-and Four-Coordinated Phosphorus
Source: Walter de Gruyter GmbH
Darstellung von 5,6-Benzo-1,3-dialkyl-2-P-substituierten 1,3,2-Diazaphosphorinan-4-onen; Einkristall-Röntgenstrukturanalysen von 2-fluorsubstituierten 1,3,2λ4-Benzodiazaphosphorinanon-Derivaten
Source: Elsevier BV
CCDC 104186: Experimental Crystal Structure Determination
Source: Cambridge Crystallographic Data Centre
Beiträge zur Chemie des 4,5-Benzo-3-methyl-1,3,2-oxazaphosphorinan- 6-on Ringsystems: Röntgenstrukturanalysen an einem Bis(2-chlorethyl)amino- und einem Acetamido-substituierten Derivat / Chemistry of the 4,5-Benzo-3-methyl-1,3,2-oxazaphosphorinan-6-one Ring System: X-Ray Crystal Structure Analysis of a Bis(2-chloroethyl)amino- and of an Acetamido-Substituted Derivative
Source: Walter de Gruyter GmbH
Mafosfamide — A Derivative of 4-Hydroxycyclophosphamide
Source: Springer Berlin Heidelberg
Novel heterocycles. 2. Synthesis of the 1,3,2‐benzodiazaphosphorin ring system
Source: Wiley

Linking provided by 

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.