Silver-Catalyzed Isocyanide Insertion into N?H Bond of Ammonia: [5+1] Annulation to Quinazoline Derivatives

Article abstract of DOI:10.1002/adsc.201701623

A silver-catalyzed [5+1] annulation of o-acylaryl isocyanides with ammonium acetate and hydroxlamine was developed for the efficient and practical synthesis of quinazolines and quinazoline 3-oxides in good to excellent yields, respectively. The domino process involved an unprecedented isocyanide insertion into the N?H bond of ammonia or hydroxylamine and followed by condensation reaction at ambient conditions. (Figure presented.).

Full text of DOI:10.1002/adsc.201701623

Title: Silver-Catalyzed Isocyanide Insertion into N–H Bond of Ammonia:
[5 + 1] Annulation to Quinazoline Derivatives
Authors: Lingjuan Zhang, Juanjuan Li, Zhongyan Hu, Jinhuan Dong,
Xian-Ming Zhang, and Xianxiu Xu
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201701623
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10.1002/adsc.201701623
Advanced Synthesis & Catalysis
COMMUNICATION
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Silver-Catalyzed Isocyanide Insertion into N–H Bond of
Ammonia: [5 + 1] Annulation to Quinazoline Derivatives
Lingjuan Zhang,a Juanjuan Li,a Zhongyan Hu,b Jinhuan Dong,b* Xian-Ming Zhang,a and
Xianxiu Xub*
a
Key Laboratory of Magnetic Molecules & Magnetic Information Materials Ministry of Education, The School of
Chemical and Material Science, Shanxi Normal University, Linfen, China, 041004
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized
b
Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of
Education, Institute of Molecular and Nano Science, Shandong Normal University, Jinan 250014, China
E-mail: dongjh@sdnu.edu.cn; xuxx677@sdnu.edu.cn
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract. A silver-catalyzed [5 + 1] annulation of o-
acylaryl isocyanides with ammonium acetate and
hydroxlamine was developed for the efficient and practical
synthesis of quinazolines and quinazoline 3-oxides in good
to excellent yields, respectively. The domino process
involved an unprecedented isocyanide insertion into the
N−H bond of ammonia or hydroxylamine and followed by
condensation reaction at ambient conditions.
Keywords: silver-catalyzed; [5 + 1] annulation; isocyanide
insertion; quinazolines; quinazoline 3-oxides
0 Due to its abundance and low cost, ammonia, one of
1 commodity chemicals, has long been recognized as
2 an ideal nitrogen source for the preparation of
3 nitrogen-containing compounds.[1] Especially, the
4 domino transformation of ammonia to assemble of
5 the valuable N-heterocycles is more appealing.
6 Quinazoline derivatives are present in a wide variety
7 of natural products and pharmaceuticals with
8 significant physiological and biological activity.[2]
9 Thus, a large number of new synthetic strategies for
10 their preparations have been developed to date.[3-9]
11 Among the existing methods, the direct assemble of
12 quinazolines using NH3 as nitrogen source attracted
26
13 much attention. In 2012, Wang and co-workers
14 developed an iodine-catalyzed oxidative amination of
27 Scheme 1. Assemble of quinazolines with ammonia
15 C(sp3)-H bonds for the synthesis of quinazolines
16 from 2-aminobenzophenones, ammonia, and N-
28 reaction
of
(2-aminophenyl)methanols
with
17 alkylamides (Scheme 1, eq 1, condition A).[4] Later,
18 the three-component reaction involving 2-
19 aminobenzophenones, aldehydes, and ammonium
20 acetate for the direct access to quinazolines was
21 independently reported by the research groups of Ma
22 (Scheme 1, eq 1, condition B),[5] Li (Scheme 1, eq
23 2),[6] Zhang (Scheme 1, eq 3, condition A),[7] Saha
24 (Scheme 1, eq 3, condition B).[8] In addition, Wu and
25 co-worker reported a copper-catalyzed cascade
29 aldehydes using the combination of cerium nitrate
30 hexahydrate and ammonium chloride for the
31 synthesis of quinazolines (Scheme 1, eq 4).[9] Despite
32 these achievements, the development of new
33 strategies for the efficient synthesis of quinazolines
34 using ammonia as nitrogen source under mild
35 conditions is still desirable.
1
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10.1002/adsc.201701623
Advanced Synthesis & Catalysis
1
Isocyanide insertion reaction has been widely63 equivalent (entries 16-17). Hence, the optimal
2 involved in the preparation of nitrogen-containing64 condition for the insertion reaction involves Ag2CO3
3 compounds.[10,11] Among these transformations6, 5 (10 mol %) in CH3CN at room temperature using
4 isocyanide insertion into N–H bonds of amines has66 ammonium acetate as N–H source (Table 1, entry 8).
5 proven to be
a promising protocol for the
6 construction of N-heterocycles.[10,12] Although the67 Table 1. Optimization of reaction conditions a
7 reactions involving isocyanide insertion into N–H
8 bonds of primary and secondary amines have been
9 reported,[12] to our knowledge, isocyanide insertion
10 into the N–H bonds of ammonia has not been
11 explored so far. We have focused our study on
68
12 isocyanide-based annulations in the synthesis of
13 heterocycles for years.[13] And very recently, we
14 developed an unprecedented chemoselective double
15 annulation of o-acylaryl isocyanides with α-
16 trifluoromethylated isocyanides for the synthesis of
17 trifluoromethylated oxadiazino[3, 2-a]indoles, in
18 which a formal isocyanide insertion into C=O is
19 involved.[14] Herein, we report a silver-catalyzed
20 domino [5 + 1] annulation of o-acylaryl isocyanides
21 with ammonium acetate for the efficient and practical
22 synthesis of quinazolines (Scheme 1, eq 5). Although
23 isocyanides have already been used to synthesize
24 quinazoline derivatives,[15] this quinazoline synthesis
25 involved the first example of isocyanide insertion into
26 N–H bonds of the commodity chemical ammonia.
Cat.
(mol % )
T.
(ºC)
Time
(h)
3aa
Entry
N source
(%) b
1
2
3
4
5
6
7
8
Ag2CO3 (30)
AgOTf (30)
AgF (30)
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH3·H2O
NH4Cl
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
80
80
80
80
60
40
25
25
25
25
25
25
25
25
25
25
25
25
25
0.25
0.25
0.25
0.25
0.5
1.5
2.0
4.0
14
4.0
4.0
4.0
4.0
4.0
4.0
24
94
72
82
48
93
93
92
92
85
60
-
83
81
71
92
-
CuCl (30)
Ag2CO3 (30)
Ag2CO3 (30)
Ag2CO3 (30)
Ag2CO3 (10)
Ag2CO3 (5)
Ag2CO3 (10)
Ag2CO3 (10)
Ag2CO3 (10)
Ag2CO3 (10)
Ag2CO3 (10)
Ag2CO3 (10)
--
9
10
11
12 c
13 d
14 e
15 f
16
17
18
19g
27 Silver
nitrate-catalyzed
insertion
of
2-
28 isocyanobenzoate into the N−H bond of primary
29 amines for the synthesis of quinazolinones were
30 developed by Zhu recently,[12a] however, only two
31 examples (with benzylamine and tryptamine) were
32 reported and the reaction was performed at 60 ºC. In
33 contrast, our domino reaction provides a general
Na2CO3 (10)
Cs2CO3 (10)
Ag2CO3 (10)
24
24
10.0
-
-
85
a)
69
reaction conditions: 1a, (0.3 mmol), NH4OAc, (0.6 mmol),
34 protocol for the synthesis of various aromatic
35 quinazolines with broad substrate scope at room
36 temperature. In addition, a series of quinazoline 3-
37 oxides were also synthesized by the same
38 transformation of o-acylaryl isocyanides and
39 hydroxylamine (Scheme 1, eq 6).
40 Originally, the exploration started with o-
41 acylphenyl isocyanide 1a and ammonium acetate 2a
42 to give the corresponding 4-phenylquinazoline 3aa to
43 optimize the reaction conditions. It was found that the
44 product 3aa can be isolated in 94% yield in the
45 presence of Ag2CO3 (30 mol %) in CH3CN under 80
46 ºC for 0.25 h (Table 1, entry 1). Selected metal salts,
47 such as AgOTf, AgF and CuCl, were also examined
48 but gave 3aa in lower yields (entries 2-4). No
49 obvious difference in terms of yield was observed
50 when decreasing the reaction temperature (entries 5-
51 7). Decreasing the amount of Ag2CO3 to 10 mol %
52 had no obvious influence on the yield of reaction
53 except slight prolonging of reaction time (entries 8
54 and 9). Then, we found that the reaction was
55 insensitive when NH3·H2O or NH4Cl was used as N–
56 H source (entries 10 and 11). Solvent screening
b)
c)
70 metal salts, (10 mol %), CH3CN, (3 mL); isolated yields;
71 EtOH as solvent; THF as solvent; DCE as solvent; N2
72 atmosphere; g) NH4OAc, (0.45 mmol).
d)
e)
f)
73
Subsequent work was to investigate the substrate
74 scopes of this efficienct and mild domino protocol
75 under the optimized condition (Scheme 2).
76 Satisfactorily, the diversity of the R1 groups including
77 electron-neutral/poor/rich aryl (Scheme 2, 1a-c) or
78 aliphatic groups (Scheme 2, 1d-g) and R2 groups
79 including electron-withdrawing/donating substituents
80 (Scheme 2, 1h-r) on isocyanides 1 were allowed. All
81 of corresponding products 3aa-3ra were obtained
82 with good to high yields. Moreover, it was noted that
83 the reaction tolerated a wide range of R2 substitutents
84 on the 5-8 positions of quinazolines (3ha-3ra).
85 Interestingly, quinazolin 4-(3H)-one 3sa was also
86 constructed in high yield using methyl 2-
87 isocyanobenzoate as substrate under the same
88 condition. Furthermore, the practicability of this
89 domino reaction was demonstrated by a gram-scale
90 synthesis of 3aa (Scheme 2, 1.142g, 92%).
91
It has been found that quinazoline N-oxides
92 frequently applied in organic synthesis and the
93 pharmaceutical industry.[16] Recently, an elegant
94 Rh(III)- and Zn(II)-catalyzed C−H amidation-
95 cyclization of oximes was developed for the synthesis
96 of quinazoline N-Oxides by Li and co-workers.[17]
57 showed that CH3CN gave the highest yield of 3aa
58 (entries 12-14). It was found that the reaction did not
59 proceed at all when silver salt was absence or
60 replaced Ag2CO3 by Na2CO3 and Cs2CO3 (entries 16-
61 18). The yield of 3aa was decreased to 85% when the
62 amount of ammonium acetate was reduced to 1.5
2
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10.1002/adsc.201701623
Advanced Synthesis & Catalysis
1 Scheme 2. Synthesis of substituted quinazolines a,b
18 condensation reaction tolerated various isocyanides 1
19 bearing arylacyl (1a-c) and alkylacyl groups (1d-f),
20 halo (1h-j, 1n, 1q and 1r) and alkyl groups (1l and 1p)
21 at ambient conditions.
22
On the basis of related reports[12,14] and the present
23 results, a possible reaction mechanism is shown in
24 Scheme 4 (exemplified by the generation of 3aa).
25 Ag2CO3 coordinates to isocyanide 1a to form
26 complex A, which coordination with ammonia
27 generates complex B. In the presence of a base,
28 migratory insertion from B affords imidoylsilver
29 intermediate C. Then, salt metathesis of C produces
30 o-carbonyl phenylamidine D, which was detected by
31 high-resolution mass spectra ([M + H]+ = 225.1025,
32 Fig. S1). Finally, the intramolecular condensation of
33 D leads to 3aa.
2
a)
3
4
5
Reaction conditions: 1a, (0.3 mmol), NH4OAc, (0.6 mmol),
Ag2CO3, (10 mol %), CH3CN, (3 mL), room temperature, 4.0 h; b)
Yield of isolated product; c) Gram-scale: 1.14 g, 92%.
34
6 To our delight, a series of quinazoline-3-oxides
7 3ab[18]-3qb were produced in good to excellent yields
8 when o-acylphenyl isocyanides 1 was treated with
9 hydroxylamine hydrochloride (NH2OH·HCl) 2b in
10 the presence of Ag2CO3 (10 mol %) and 2.0 equiv of
35 Scheme 4. Plausible mechanism.
36
In summary, an efficient and practical method for
37 the construction of polysubstituted quinazolines and
38 quinazoline 3-oxides under ambient conditions has
39 been successfully disclosed. This domino process
11 diethylamine (Scheme 3). This domino isocyanide
12 insertion into N−H bond of hydroxylamine and
13 Scheme 3. Synthesis of quinazoline-3-oxides a,b
40 involves
an
unprecedented
silver-catalyzed
41 isocyanide insertion into the N–H bonds of ammonia
42 or hydroxylamine and an intramolecular condensation
43 reaciton. This reaction features mild reaction
44 conditions, operational simplicity, high to excellent
45 product yields and amenability to gram-scale
46 synthesis. Investigations on new isocyanide insertion
47 reactions are ongoing.
48 Experimental Section
49 General procedure for the synthesis of 3a: To a mixture
50 of (2-isocyanophenyl)(phenyl)methanone (1) (0.3 mmol)
51 and ammonium acetate (2a) (46.7 mg, 0.6 mmol) in
52 CH3CN (3 mL) at 25 ºC was added Ag2CO3 (8.8 mg, 0.03
53 mmol). After the reaction was finished as indicated by
54 TLC (4 h), the resulting mixture was poured into water (10
55 mL) and extracted with EtOAc (6 mL × 3). The combined
56 organic layer was dried over anhydrous Na2SO4 and
57 concentrated in vacuo. Purification of the crude product
58 with flash column chromatography to give 3a.
59 Acknowledgements
14
a)
15
reaction conditions: 1a, (0.3 mmol), NH2OH·HCl, (0.6 mmol),
16 Ag2CO3, (10 mol %), HN(Et)2, (0.6 mmol), CH3CN, (3 mL), 1.5
60 Financial support provided by NSFC (21402112,
61 21672034) and 1331 project of Shanxi Province is
62 gratefully acknowledged.
17 h; b) Yield of isolated product. c) ND = not detected.
3
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Advanced Synthesis & Catalysis
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4
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10.1002/adsc.201701623
Advanced Synthesis & Catalysis
COMMUNICATION
Silver-Catalyzed Isocyanide Insertion into N–H
Bond of Ammonia: [5 + 1] Annulation to
Quinazoline Derivatives
Adv. Synth. Catal. 2017, Volume, Page – Page
Lingjuan Zhang,a Juanjuan Li,a Zhongyan Hu,b
Jinhuan Dong,b* Xian-Ming Zhang,a and Xianxiu
Xub*
5
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