Surface-mediated synthesis of organophosphorus-based hydrazides using basic alumina

Article abstract of DOI:10.1139/V10-111

The surface-mediated synthesis of O-alkyl alkylphosphorohydrazides and N,N-dialkylamino alkylphosphorohy- drazides from phosphoryl chlorides is described. The effect of the presence of chromatographic-grade Al ₂O₃ (basic) on the hydr

Full text of DOI:10.1139/V10-111

1034
Surface-mediated synthesis of
organophosphorus-based hydrazides using basic
alumina
Kavita, P. Joshi, N. Sharma, and Y.C. Joshi
Abstract: The surface-mediated synthesis of O-alkyl alkylphosphorohydrazides and N,N-dialkylamino alkylphosphorohy-
drazides from phosphoryl chlorides is described. The effect of the presence of chromatographic-grade Al2O3 (basic) on the
hydrazinolysis of a series of O-alkyl alkylphosphonic chlorides and N,N-dialkylamino alkylphosphonic chlorides has also
been investigated. It was observed that higher yields of the less-hindered hydrazides were obtained
Key words: O-alkyl alkylphosphonic chlorides, N,N-dialkylamino alkylphosphoric chlorides, phosphorohydrazides, surface
mediated, Al2O3 (basic).
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Resume : On decrit une methode de synthese catalysee par la surface de O-alkylphosphorohydrazides et de N,N-dialkyl-
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aminoalkylphosphorohydrazides a partir de chlorures du phosphoryle. On a aussi etudie l’effet de la presence d’alumine,
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Al2O3 (basique), de qualite chromatographique sur l’hydrazinolyse d’une serie de chlorures d’acides O-alkyl alkylphospho-
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niques et d’acides N,N-dialkylamino alkylphosphoniques. Il a ete observe que les rendements obtenus sont plus eleves
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avec les hydrazides les moins encombrees.
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Mots-cles : chlorures d’acides O-alkyl alkylphosphoniques, chlorures d’acides N,N-dialkylamino alkylphosphoniques,
Al2O3 (basique).
of execution and work-ups, mild reaction conditions, fast
Introduction
rate of reactions, selectivity, higher yields, solvent-less reac-
tion conditions, and low cost in comparison with their ho-
mogeneous counterparts.21–23 Chromatographic grade Al2O3
(basic) has many applications as a heterogeneous catalyst ei-
ther by itself or, more commonly, as a support for other re-
agents.20 There have been only a few reports, however, on
the use of Al2O3 as a support for substrates, despite the fact
that novel, synthetically useful, reactions have been ob-
served under these conditions. Symmetrical functional sub-
strates adsorb to the surface of Al2O3 via a functional
group. The other reactant selectively attaches to the alumina
surface by reaction with the free functional group. This
prompted us to explore the utility of a surface-mediated re-
action for the synthesis of title compounds, in continuation
of our ongoing research program to develop new synthetic
methods for antibacterial compounds.24 We have synthesized
various O-alkyl alkylphosphorohydrazides and N,N-dialkyl-
aminophosphonohydrazides 3a–3p.
The chemistry of organophosphorus compounds is a rap-
idly developing area of research because of their importance
in industrial, agricultural, biochemical, and medicinal appli-
cations.1 It is interesting to note that the variation in their
physical, chemical, and biological properties is governed by
the selection of the group attached to the phosphorus atom.
Although phosphorous compounds containing the P–C bond
are not abundant in nature, they have diverse range of bio-
logical activity and have attracted considerable synthetic
and pharmacological interest.2
Hydrazides are versatile intermediates for the synthesis of
hydrazones,3 pyrazoles,4 and various heterocyclic com-
pounds.5 It is well known that hydrazides play an important
role in antimicrobial activity. Furthermore, a number of hy-
drazide derivatives have been reported to possess interesting
antibacterial,antifungal,6–8 anticonvulsant,9,10 anti-inflamma-
tory,11,12 antimalarial,13 and antituberculosis activities.3,14–18
Several methods have been reported in the literature for
the synthesis of hydrazides.19 However, the synthesis of
phosphorohydrazides has not been fully explored. There
have been only a few reports on the synthesis of phosphoro-
hydrazides, and these have several drawbacks such as the
use of carcinogenic solvents, long reaction times, and forma-
tion of several by-products.
Results and discussion
To test the above proposition, we have carried out the re-
action of alkyl phosphonic dichloride 125 with various alco-
hols and amines in the presence of triethylamine at 0 8C
followed by heating at 50 8C. This reaction gave O-alkyl-
and N,N-dialkylamino alkylphosphonic chlorides 2a–2p.26
After obtaining the intermediates 2a–2p, we optimized the
Surface-mediated solid-phase reactions are of growing in-
terest20 in the synthesis of hydrazides because of their ease
Received 3 March 2010. Accepted 20 July 2010. Published on the NRC Research Press Web site at canjchem.nrc.ca on 2 October 2010.
Kavita,1 N. Sharma, and Y.C. Joshi. Department of Chemistry, University of Rajasthan, Jaipur 302004, India.
P. Joshi. S.S. Jain Subodh P.G. College, Jaipur, India.
1Corresponding author (e-mail: drkavitaraj@rediffmail.com).
Can. J. Chem. 88: 1034–1039 (2010)
doi:10.1139/V10-111
Published by NRC Research Press

Kavita et al.
1035
Scheme 1. Proposed mechanism for the synthesis of phosphonohydrazides on alumina.
reaction conditions to obtain phosphorohydrazides. In this
regard, several reactions of O-methyl isopropylphosphonic
chloride with various reagents such as neutral Al2O3, basic
Al2O3, acidic Al2O3, SiO2, ZnO, and ZnO–SiO2 were per-
formed as model reactions. Maximum yield was obtained
when basicAl2O3 was used. Further, to optimize the molar
ratio of basic Al2O3, various reactions of O-methyl isopro-
pylphosphonic chloride were also performed by changing
the mole ratio of basic Al2O3, reaction time, and tempera-
ture. These reactions were monitored through TLC and 31P
NMR. Best results were obtained when the model reaction
was performed with basic Al2O3 and O-methyl isopropyl-
phosphonic chloride in the mole ratio of 1:1 at 60 8C for
30 min.
H3PO4 as an external standard for 31P NMR. Mass spectra
were performed on a LCMS. Satisfactory C, H, N analyses
were obtained for all the compounds.
General procedure for the preparation of O-methyl
isopropylphosphorohydrazide 3a
In a typical experimental procedure, basic activated alu-
mina (1.0 g, 0.01 mol/L) was mixed with hydrazine hydrate
99% (0.32 g, 0.01 mol/L) in a mortar and pestler. It was
ground for 5 min. at room temperature. The mixture was
transferred into a single-necked flask and sealed with rubber
septum, and then O-methyl isopropylphosphonic chloride
(1.55 g, 0.01 mol/L) was added through a syringe at 0 8C.
The resultant dispersion was shaken occasionally at room
temperature followed by heating at 60 8C for 30 min. The
reaction mixture was monitored using TLC and GC by
drawing a few milligrams of the mixture and suspending it
in 1 mL of diethyl ether. After completion of the reaction,
the reaction mixture was extracted in dichloromethane and
filtered. The solvent was removed and the residue was crys-
tallized with diethyl ether.
O-Methyl isopropylphosphorohydrazide 3a
IR nmax (cm–1): 3320, 3265 (N–H), 3140 (N–H), 2890 (C–
1
H), 1235 (P=O), 1090 (P–O–C), 695 (P–C). H NMR d: 1.10
(dd, 3J(PH) = 21.4 Hz, 6H, CH3), 2.05 (m, 2J(PH) =
After optimization, the general applicability of the method
was applied with diversity in structures 2a–2p and results of
the reactions are summarized in Table1. All the compounds
3a–3p were characterized by spectroscopic techniques such
as FTIR, 31P NMR, LC–MS, and elemental analysis. The
FTIR spectra showed the presence of NH bands at 3320,
3260 (NH2), and 3140 (sec-amine). It is worth noticing that
the 31P NMR signal of O-alkyl alkylphosphonochloridates
2a–2p disappeared and a new signal appeared in the range
of 19–42 ppm for 3a–3p. The results of other analysis 3a–
3p are compiled in the Experimental section.
3
17.3 Hz, 1H, CH), 2.92 (br s, 2H, NH2), 3.95 (s, J(PH) =
2
19.4 Hz, 3H, CH3), 4.22 (d, J(PH) = 18.5 Hz, 1H, NH).
13C NMR d: 15.85 (CH3), 26.78 (CH), 62.58 (CH3). LCMS
(EI) m/z: 153 (M + H+). Anal. calcd. for C4H13N2O2P: C
31.58, H 8.61, N 18.41; found: C 31.50, H 8.58, N 18.35.
O-Ethyl isopropylphosphorohydrazide 3b
IR nmax (cm–1): 3325, 3260 (N–H), 3145 (N–H), 2885 (C–
1
H), 1230 (P=O), 1090 (P–O–C), 697 (P–C). H NMR d: 1.05
3
(dd, J(PH) = 21.4 Hz, 6H, CH3), 1.15 (t, J = 7.8 Hz, 3H,
2
CH3), 2.05 (m, J(PH) = 17.5 Hz, 1H, CH), 2.95(br s, 2H,
3
2
NH2), 3.90 (q, J(PH) = 19.7 Hz, 2H, CH2), 4.20 (d, J(PH) =
18.5 Hz, 1H, NH). 13C NMR d: 15.85 (CH3), 17.25 (CH3),
26.78 (CH), 62.58 (CH2). LCMS (EI) m/z: 167 (M + H+).
Anal. calcd. for C5H15N2O2P: C 36.14, H 9.10, N 16.86;
found: C 36.15, H 9.05, N 16.83.
Experimental
General
Melting points were determined on a hot stage micro-
scope and are uncorrected. IR spectra were recorded on
FTIR spectrometer model Jasco 610 on KBr pellets. 1H, 13 C,
and 31P NMR spectra were recorded in CDCl3 on Bruker
FTNMR at 400, 100, and 162 MHz, respectively, using tet-
ramethylsilane as an internal standard for 1H and 85%
O-Propyl isopropylphosphorohydrazide 3c
IR nmax (cm–1): 3320, 3270 (N–H), 3150 (N–H), 2905 (C–
1
H), 1240 (P=O), 1085 (P–O–C), 705 (P–C). H NMR d: 0.95
Published by NRC Research Press

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Can. J. Chem. Vol. 88, 2010
Table 1. Synthesis of O-alkyl alkylphosphoro- and N,N-dialkylaminophosphonohydrazides (3a–3p).
Published by NRC Research Press

Kavita et al.
1037
3
(t, J = 7.8 Hz, 3H, CH3), 1.10 (dd, J(PH) = 21.5 Hz, 6H,
NH), 7.25–7.50 (m, 5H, C6H5). 13C NMR d: 15.85 (CH3),
62.58 (CH), 172–178 (Ar–C). LCMS (EI) m/z: 215 (M +
H+). Anal. calcd. for C9H15N2O2P: C 50.46, H 7.06, N
13.08; found: C 50.45, H 7.10, N 13.05.
2
CH3), 1.15 (m, J = 7.9 Hz, 3H, CH2), 2.05 (m, J(PH) =
17.5 Hz, 1H, CH), 3.07 (br s, 2H, NH2), 3.95 (q, J(PH) =
3
2
19.4 Hz, 2H, CH2), 4.25 (d, J(PH) = 18.7 Hz, 1H, NH).
13C NMR d: 15.93 (CH3), 17.23 (CH3), 22.58 (CH2), 26.80
(CH), 62.70 (CH2). LCMS (EI) m/z: 181 (M + H+). Anal.
calcd. for C6H17N2O2P: C 39.99, H 9.15, N 15.55; found: C
39.95, H 9.17, N 15.53.
O-Isobutyl phenylphosphorohydrazide 3i
IR nmax (cm–1): 3320, 3260 (N–H), 3140 (N–H), 2890 (C–
H), 1235 (P=O), 1090 (P–O–C), 695 (P–C). 1H NMR d:
1.15(d, J = 6.5 Hz, 6H, CH3), 1.20 (sextet, J = 6.5 Hz, 1H,
O-Butyl isopropyl phosphorohydrazide 3d
IR nmax (cm–1): 3315, 3240 (N–H), 3160 (N–H), 2897 (C–
3
CH), 2.85 (br s, 2H, NH2), 4.15 (sextet, J(PH) = 19.4 Hz,
3
2H, CH2), 4.22 (d, J(PH) = 18.5 Hz, 1H, NH), 7.25–7.88
1
(m, 5H, C6H5). 13C NMR d: 15.68 (CH3), 22.50 (CH), 62.58
(CH2), 172–178 (Ar–C). LCMS (EI) m/z: 229 (M + H+).
Anal. calcd. for C10H17N2O2P: C 52.63, H 7.51, N 12.27;
found: C 52.65, H 7.50, N 12.28.
H), 1239 (P=O), 1090 (P–O–C), 697 (P–C). H NMR d: 0.95
3
(t, J = 8.2 Hz, 3H, CH3), 1.07 (dd, J(PH) = 22.3 Hz, 6H,
CH3), 1.15 (m, J = 7.9 Hz, 3H, CH2), 1.28 (m, J = 7.6 Hz,
3H, CH2), 2.05 (m, J(PH) = 17.3 Hz, 1H, CH), 2.92 (br s,
2
3
2H, NH2), 4.05 (q, J(PH) = 19.4 Hz, 2H, CH2), 4.27 (d,
2J(PH) = 18.5 Hz, 1H, NH). 13C NMR d: 15.80 (CH3),
17.23 (CH3), 23.60 (CH2), 25.85 (CH2), 26.98 (CH), 62.45
(CH2). LCMS (EI) m/z: 195 (M + H+). Anal. calcd. for
C7H19N2O2P: C 43.29, H 9.86, N 14.42; found: C 43.30, H
9.81, N 14.43.
O-Pentyl phenylphosphorohydrazide 3j
IR nmax (cm–1): 3309, 3256 (N–H), 3143 (N–H), 2908 (C–
1
H), 1255 (P=O), 1070 (P–O–C), 693 (P–C). H NMR d: 0.95
(t, J =7.8 Hz, 3H, CH3), 1.15 (m, J = 8.6 Hz, 3H, CH2), 1.23
(m, J = 8.1 Hz, 3H, CH2), 1.37 (m, J = 7.4 Hz, 3H, CH2),
3
2.92 (br s, 2H, NH2), 3.97(q, J(PH) = 19.4 Hz, 2H, CH2),
O-Pentyl isopropylphosphorohydrazide 3e
2
4.56 (d, J(PH) = 18.9 Hz, 1H, NH), 7.25–7.50 (m, 5H,
IR nmax (cm–1): 3325, 3260 (N–H), 3170 (N–H), 2907 (C–
C6H5). 13C NMR d: 15.83 (CH3), 21.89 (CH2), 22.38 (CH2),
25.75 (CH2), 63.03 (CH2), 172–178 (Ar–C). LCMS (EI) m/z:
243 (M + H+). Anal. calcd. for C8H21N2O2P: requires C
54.54, H 7.91, N 11.56; found: C 54.52, H 7.93, N 11.55.
H), 1245 (P=O), 1095 (P–O–C), 705(P–C). 1H NMR d:
3
0.95(t, J = 7.9 Hz, 3H, CH3), 1.07 (dd, J(PH) = 21.4 Hz,
6H, CH3), 1.18 (m, J = 7.3 Hz, 3H, CH2), 1.25 (m, J =
8.5 Hz, 3H, CH2), 1.35 (m, J = 8.3 Hz, 3H, CH2), 2.05 (m,
2J(PH) = 17.6 Hz, 1H, CH), 2.92 (br s, 2H, NH2), 3.95(q,
N,N-Diethylamino isopropylphosphonohydrazide 3k
IR nmax (cm–1): 3340, 3265 (N–H), 3150 (N–H), 2910 (C–
H), 1460 (C–N), 1245 (P=O), 1070, 1155 (P–N–C), 705 (P–
3J(PH) = 19.5 Hz, 2H, CH2), 4.15 (d, J(PH) = 18.2 Hz,
2
1H, NH). 13C NMR d: 15.90 (CH3), 17.20 (CH3), 21.89
(CH2), 22.26 (CH2), 25.85 (CH2), 26.58 (CH), 62.54 (CH2).
1
C). H NMR d: 1.03 (t, J = 8.4 Hz, 6H, CH3), 1.15(dd,
LCMS (EI) m/z: 209 (M
+
H+). Anal. calcd. for
2
3J(PH) = 22.5 Hz, 6H, CH3), 1.85 (m, J(PH) = 16.7 Hz,
C8H21N2O2P: C 46.14, H 10.16, N 13.45; found: C 46.15, H
10.15, N 13.43. .
3
1H, CH), 2.60 (br s, 2H, NH2), 3.65 (q, J(PH) = 19.4 Hz,
2
4H, CH2), 4.25 (d, J(PH) = 17.9 Hz, 1H, NH). 13C NMR d:
16.88 (CH3),17.37 (CH3), 26.98 (CH), 42.58 (CH2). LCMS
(EI) m/z: 194 (M + H+). Anal. calcd. for C7H20N3OP: C
45.51, H 10.43, N 21.75; found: C 45.50, H 10.45, N 21.73.
O-Ethyl phenylphosphorohydrazide 3f
IR nmax (cm–1): 3320, 3260 (N–H), 3140 (N–H), 2890 (C–
1
H), 1235 (P=O), 1090 (P–O–C), 695 (P–C). H NMR d: 1.15
3
(t, J(PH) = 21.4 Hz, 3H, CH3), 2.85 (br s, 2H, NH2), 4.15
N,N-Dipropylamino isopropylphosphonohydrazide 3l
IR nmax (cm–1): 3327, 3265 (N–H), 3146(N–H), 2920 (C–
H), 1435 (C–N), 1235 (P=O), 1080, 1150 (P–N–C), 703 (P–
3
3
(q, J(PH) = 19.4, 2H, CH2), 4.22 (d, J(PH) = 18.5 Hz, 1H,
NH), 7.25–7.50 (m, 5H, C6H5). 13C NMR d: 15.85 (CH3),
62.58 (CH2), 172–178 (Ar–C). LCMS (EI) m/z: 201 (M +
H+). Anal. calcd. for C8H13N2O2P: C 48.00, H 6.55, N
13.99; found: C 48.05, H 6.51, N 13.95.
1
C). H NMR d: 0.75 (t, J = 8.4 Hz, 6H, CH3), 1.15 (dd,
3J(PH) = 21.9 Hz, 6H, CH3), 1.45 (m, 4H, CH2), 1.95 (m,
2J(PH) = 17.3 Hz, 1H, CH), 3.15 (br s, 2H, NH2), 3.85 (q,
2
3J(PH) = 19.8 Hz, 4H, CH2), 3.98 (d, J(PH) = 16.5 Hz,
O-Propyl phenylphosphorohydrazide 3g
IR nmax (cm–1): 3320, 3260 (N–H), 3140 (N–H), 2890 (C–
H), 1235 (P=O), 1090 (P–O–C), 695 (P–C). H NMR d: 1.15
1H, NH). 13C NMR d: 15.67 (CH3), 17.20(CH3), 22.45
(CH2), 27.03 (CH), 41.37 (CH2). LCMS (EI) m/z: 222 (M +
H+). Anal. calcd. for C7H20N3OP: C 48.85, H 10.93, N
18.99; found: C 48.86, H 10.95, N 18.96.
1
(t, J = 6.5 Hz, 3H, CH3), 1.35 (q, J = 7.4 Hz, 2H, CH2), 2.85
3
(br s, 2H, NH2), 4.15 (q, J(PH) = 19.4 Hz, 2H, CH2), 4.22
(d,3J(PH) = 18.5 Hz, 1H, NH), 7.25–7.50 (m, 5H, C6H5).
13C NMR d: 15.85 (CH3), 22.53 (CH2), 62.58 (CH2), 172–
178 (Ar–C). LCMS (EI) m/z: 215 (M + H+). Anal. calcd.
for C9H15N2O2P: C 50.46, H 7.06, N 13.08; found: C 50.45,
H 7.10, N 13.05.
N,N-Dibutylamino isopropylphosphonohydrazide 3m
IR nmax (cm–1): 3320, 3260 (N–H), 3150 (N–H), 2920 (C–
H), 1447 (C–N), 1230 (P=O), 1070, 1150 (P–N–C), 693 (P–
1
C). H NMR d: 0.75 (t, J = 8.4 Hz, 6H, CH3), 1.10 (dd,
3J(PH) = 21.8 Hz, 6H, CH3), 1.40 (m, 4H, CH2), 1.55 (m,
2
O-Isopropyl phenylphosphorohydrazide 3h
IR nmax (cm–1): 3320, 3260 (N–H), 3140 (N–H), 2890 (C–
H), 1235 (P=O), 1090 (P–O–C), 695 (P–C). H NMR d: 1.15
4H, CH2), 1.97 (m, J(PH) = 16.9 Hz, 1H, CH), 2.92 (bd s,
3
2H, NH2), 3.15 (q, J(PH) =18.4 Hz, 4H, CH2), 4.20 (d,
2J(PH) =17.5 Hz, 1H, NH). 13C NMR d: 15.85 (CH3),
17.23(CH3), 20.45(CH2), 22.45(CH2), 26.78 (CH), 42.58
(CH2). LCMS (EI) m/z: 250 (M + H+). Anal. calcd. for
1
(d, J = 6.5 Hz, 6H, CH3), 2.85 (br s, 2H, NH2), 4.15 (sextet,
3
3J(PH) = 19.4 Hz, 2H, CH), 4.22 (d, J(PH) = 18.5 Hz, 1H,
Published by NRC Research Press

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Can. J. Chem. Vol. 88, 2010
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5234(99)00129-4.
C7H20N3OP: C 52.99, H 11.32, N 16.85; found: C 52.95, H
11.33, N 16.86.
N,N-Diethylamino phenylphosphonohydrazide 3n
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IR nmax (cm–1): 3320, 3260 (N–H), 3140 (N–H), 2890 (C–
H), 1457 (C–N), 1239 (P=O), 1070, 1150 (P–N–C), 695 (P–
1
C). H NMR d: 1.03 (t, J = 8.4 Hz, 6H, CH3), 2.92 (br s,
3
2H, NH2), 3.95 (q, J(PH) = 17.3 Hz, 4H, CH2), 4.15 (d,
2J(PH) = 17.6 Hz, 1H, NH), 7.25–7.58 (m, 5H, C6H5). 13C
NMR d: 17.23 (CH3), 42.58 (CH2), 172–178.27 (Ar–C).
LCMS (EI) m/z: 228 (M
+
H+). Anal. calcd. for
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C10H18N3OP: C 52.85, H 7.98, N 18.49; found: C 52.87, H
7.96, N 18.47.
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N,N-Dipropylamino phenylphosphonohydrazide 3o
IR nmax (cm–1): 3320, 3260 (N–H), 3140 (N–H), 2890 (C–
H), 1450 (C–N), 1235 (P=O), 1070, 1150 (P–N–C), 695 (P–
1
C). H NMR d: 0.75 (t, J = 8.4 Hz, 6H, CH3), 1.45 (m, 4H,
3
CH2), 2.92 (br s, 2H, NH2), 3.95 (q, J(PH) = 19.4 Hz, 4H,
2
CH2), 4.22 (d, J(PH) = 18.5 Hz, 1H, NH), 7.25–7.50 (m,
5H, C6H5). 13C NMR d: 17.23 (CH3), 22.45 (CH2), 42.15
(CH2), 172–178 (Ar–C). LCMS (EI) m/z: 256 (M + H+).
Anal. calcd. for C12H22N3OP: C 56.46, H 8.69, N 16.46;
found: C 56.48, H 8.67, N 16.44.
N,N-Dibutylamino phenylphosphonohydrazide 3p
IR nmax (cm–1): 3315, 3250 (N–H), 3135 (N–H), 2895 (C–
H), 1450 (C–N), 1235 (P=O), 1070, 1150 (P–N–C), 695 (P–
1
C). H NMR d: 0.75 (t, J = 8.4 Hz, 6H, CH3), 1.45 m, 4H,
CH2), 1.55 (m, 4H, CH2), 3.10 (br s, 2H, NH2), 2.95 (q,
2
3J(PH) = 18.6 Hz, 4H, CH2), 4.10 (d, J(PH) = 17.5 Hz,
1H, NH), 7.25–7.50 (m, 5H, C6H5). 13C NMR d: 15.85
(CH3), 17.28 (CH3), 20.49 (CH2), 22.47 (CH2), 26.78 (CH),
42.58 (CH2), 172–178 (Ar–C). LCMS (EI) m/z: 284 (M +
H+). Anal. calcd. for C14H26N3OP: C 59.34, H 9.25, N
14.83; found: C 59.35, H 9.23, N 14.80.
`
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Conclusion
In conclusion, we have developed a rapid and efficient
method for the synthesis of O-alkyl alkylphosphorohydra-
zides and N,N-dialkyl aminophosphonohydrazides 3a–3p
with excellent yields.
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