Synthesis of a Novel Class of β-Lactam Derivatives of 1-Aminophosphonates by Staudinger Ketene-Imine [2+2]-Cycloaddition Reaction

被引：2

作者：

Kaboudin, Babak ^{[1
]}

Afsharinezhad, Mohammad Bagher ^{[1
]}

机构：

[1] IASBS, Dept Chem, Zanjan 4513766731, Iran

来源：

SYNTHESIS-STUTTGART | 2010年 / 20期

关键词：

1-aminophosphonates; beta-lactams; ketenes; imines; 2+2]-cycloaddition reaction; ACID-ANALOGS; ASYMMETRIC-SYNTHESIS; PHOSPHONOPEPTIDES; PHOSPHONATES; INHIBITORS; PHOSPHITE;

D O I：

10.1055/s-0030-1257889

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel class of beta-lactam derivatives of 1-aminophosphonates was synthesized by Staudinger [2+2] cycloaddition reaction of ketenes with imines derived from 1-aminophosphonates. Treatment of aromatic aldehydes with ammonia and diethyl phosphite followed by a reaction with ketenes, which are generated from the appropriate acid chloride and a tertiary amine, gave a novel class of beta-lactam derivatives of 1-aminophosphonates. The major or, in some cases, sole product of the cycloaddition is the cis-beta-lactam.

引用

页码：3504 / 3508

页数：5

共 50 条

[11] Prediction of Theoretical Physicochemical Properties and One-Pot Synthesis of Bis-Azetidinones by [2+2] Ketene - Imine Cycloaddition in the Presence of Montmorillonite
Pagadala, Ramakanth
Meshram, Jyotsna S.
Chopde, Himani N.
Jetti, Venkateshwarlu
Kusampally, Uppalaiah
Udayini, V.
MEDICINAL CHEMISTRY, 2011, 7 (04) : 325 - 332
[12] Theoretical Study for the [2+2] Cycloaddition Reaction Mechanism of Ketenes and their Derivatives
Mohammad-Salim, Haydar A.
Abdallah, Hassan H.
ORIENTAL JOURNAL OF CHEMISTRY, 2019, 35 (05) : 1550 - 1556
[13] CHEMISTRY OF MUCOHALIC ACIDS .7. ASYMMETRIC-SYNTHESIS OF BETA-LACTAM DERIVATIVES BY THE KETENE IMINE CYCLOADDITION UTILIZING CHIRAL MUCOCHLORIC ACID-DERIVATIVES
DUCZEK, W
JAHNISCH, K
KUNATH, A
RECK, G
WINTER, G
SCHULZ, B
LIEBIGS ANNALEN DER CHEMIE, 1992, (08): : 781 - 787
[14] Toward a Novel Approach to Bis-β-Lactam Synthesis Using Vilsmeier Reagent as an Efficient Entity via Staudinger Cycloaddition Reaction
Meshram, Jyotsna
Ali, Parvez
Tiwari, Vandana
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (06) : 1454 - 1458
[15] Synthesis of Fused Indoline-Cyclobutanone Derivatives via an Intramolecular [2+2] Cycloaddition
Neyyappadath, Rifahath M.
Greenhalgh, Mark D.
Cordes, David B.
Slawin, Alexandra M. Z.
Smith, Andrew D.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) : 5169 - 5174
[16] New applications of the imine-ketenimine intramolecular [2+2] cycloaddition reaction:: Highly stereocontrolled synthesis of azeto[1,2-a]pyrimidines
Alajarín, M
Vidal, A
Orenes, RA
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (24) : 4222 - 4227
[17] Expeditious Synthesis of Novel β-Lactam-Substituted Polycyclic Fused Chromeno Pyrrole Derivatives from MBH Carbonates by Intramolecular [3+2]-Cycloaddition Reaction
Rajesh, Raju
Raghunathan, Raghavachary
SYNLETT, 2013, 24 (16) : 2107 - 2113
[18] Guidelines for β-Lactam Synthesis: Glycal Protecting Groups Dictate Stereoelectronics and [2+2] Cycloaddition Kinetics
Balijepalli, Anant S.
McNeely, James H.
Hamoud, Aladin
Grinstaff, Mark W.
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (19) : 12044 - 12057
[19] A tactical approach for the synthesis of novel β-lactam-substituted, polycyclic-fused isoxazolidine derivatives via an intramolecular [3+2] cycloaddition reaction
Rajesh, R.
Suresh, M.
Raghunathan, R.
TETRAHEDRON LETTERS, 2014, 55 (03) : 699 - 705
[20] Intramolecular [2+2]-Cycloaddition in the Synthesis of Polycyclic Tetrahydrothiopyran Derivatives Bearing a Cyclobutane Scaffold
Grzelak, Paulina
Saktura, Maciej
Sieron, Leslaw
Albrecht, Lukasz
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (10) : 2274 - 2279

← 1 2 3 4 5 →