Multiple-functionalizations of terminal alkynes with sodium sulfinates and tert-butyl nitrite: facile synthesis of 2H-azirines

Article abstract of DOI:10.1039/C9CC00625G

A new, catalyst-free tandem annulation route to 2,2-disulfonyl-2H-azirines via multiple-functionalizations of terminal alkynes with sodium sulfinates and tert-butyl nitrite is described. The use of sodium sulfinates and tert-butyl nitrite enables the form

Full text of DOI:10.1039/C9CC00625G

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DOI: 10.1039/C9CC00625G
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Multiple‐Functionalizations of Terminal Alkynes with Sodium
Sulfinates and tert‐Butyl Nitrite: Facile Synthesis of 2H‐Azirines
Xingyi He,a Xin Yue,a Lei Zhang,a Shuang Wu,a Ming Hu*,a and Jin‐Heng Li*abc
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
A new, catalyst‐free tandem annulation access to 2,2‐disulfonyl‐
2H‐azirines via multiple‐functionalizations of terminal alkynes
with sodium sulfinates and tert‐butyl nitrite is described. The use
of sodium sulfinates and tert‐butyl nitrite enables the formation
of sulfonyl and NO radicals to selectively initiate and terminate
the tandem annulation protocol, constituting a straightforward,
conceptually different method to existing 2H‐azirine synthesis
techniques that are currently required multiple steps by prior
activation of the common starting materials.
Scheme 1. Important examples of biologically active 2H‐azirines.
single reaction toward these structures is strongly appealing.
Recently, annulation of common starting materials (e.g., alkynes)
for the construction of the aziridine skeletons in one pot was
proven to be particularly attractive.7 Yet, examples of such available
transformations are rare, and the ability to effectively control the
simultaneous incorporation of a new external nitrogen fragment
and the other functional reagents across a simple alkyne in a single
reaction remains an elusive goal in synthetic endeavors. In 2015, Liu
and co‐workers7a developed a room temperature, one‐pot access to
CF3‐containing azirines in two steps by copper‐catalyzed
trifluoromethylazidation with simple there‐component starting
materials (terminal alkynes, Togni’s reagent and TMSN3) followed
by a photocatalyzed rearrangement. Meanwhile, Liang and co‐
2H‐Azirines represent important N‐heterocyclic compounds that
are
ubiquitously
encountered
in
natural
products,
pharmaceuticals, agrochemicals and organic materials (Scheme
1).1 In addition, 2H‐azirines have proved to be versatile
precursors of nitrenes, electrophiles, dienophiles, and
dipolarophiles that are widely utilized to synthesize complex
nitrogen‐containing non‐cyclic molecules and various azacyclic
compounds, such as pyrroles, indoles, pyrazolo[1,5‐a]pyridines,
oxazoles, isoxazoles and piperidines.2 Inspired by their broad
utility, many practical methods have been established, such as
the Neber reaction of imine substrates (Scheme 2a),3
thermal/photochemical rearrangement of vinyl azides (Scheme
2b),4 ring contraction of isoxazole/oxazaphosphole derivatives
(Scheme 2c)5 and elimination/oxidation of aziridines (Scheme workers have reported a similar copper catalysis which enables the
2d).6 Such precedents remain a challenge of the requirement of
pre‐functionalized starting materials that are generated from
the reaction of common chemicals (e.g., alkynes, alkenes,
carbonyls) with the nitrogen source reagents, thereby offering
formation of CF3‐containing azirines in a single reaction promoted
by NaOAc base under heating (80 oC).7b The Liang group7c and
Yu/Han group7d have independently extended this copper catalysis
to annulation cascades of enynes with Togni’s reagent and TMSN3
for producing complex functionalized aziridines in one step with the
aid of heating (60 to 90 oC).
Herein, we report a new annulation reaction of terminal
alkynes with sodium sulfinates using tert‐butyl nitrite as nitrogen
source8 for the synthesis of functionalized 2H‐azirines (Scheme 2e).
This method is distinguished by its success achieved through the
use of common, most commercial available starting materials under
mild, catalyst‐free conditions, as well as by its exquisite chemo‐ and
site‐selectivity, thus allowing the formation of 2,2‐disulfonyl‐2H‐
azirines via multiple‐functionalizations of terminal alkynes.
Our investigations began by assessing three‐component
tandem annulation of 1‐bromo‐4‐ethynylbenzene (1a) with sodium
limited
functional
2H‐azirine
frameworks.
Therefore,
development of general strategies that utilize common,
especially commercial available starting materials directly in a
a.Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources
Recycle, Nanchang Hangkong University, Nanchang 330063, China
b.State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University,
Changsha 410082, China
c.State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou
730000, China
E‐mail: huming0731@163.com and jhli@hnu.edu.cn
† Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
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2H‐azirines (Table 2). In the presence of sulfinate 2a VainewdAtr‐tiBclueOONnliOne,
DOI: 10.1039/C9CC00625G
a wide range of aryl alkynes 1b‐k, 1q‐w and alkyl analogues 1l‐p
could be utilized as substrates, giving the targeted 2H‐azirine 3ba‐
wa in moderate to good yields. For common arylalkynes, an array of
substituents, including Me, MeO, Cl, CN, and NO2, on the aryl ring
were tolerated well, and both the electronic nature and position
affected the reactivity (3ba‐ia). Alkynes 1b‐d, possessing electron‐
rich C6H5, p‐MeC6H4 and p‐MeOC6H4 groups, respectively, were
converted efficiently into 3ba‐da in 72‐78% yields. Whereas alkynes
1f‐g with an electron‐deficient group (e.g., p‐CNC6H4 and p‐NO2C6H4)
delivered 3fa‐ga in diminishing yields. The reactivity of Me‐
substituted arylalkynes 1c, 1h‐i decreased from para (3ca) to meta
(3ha) to ortho substitution (3ia) in terms of yields. Both 1‐
ethynylnaphthalene 1j and 3‐ethynylthiophene 1k were viable
substrates (3ja‐ka). Using ethynylcyclohexane 1l allowed the
formation of 3la smoothly. Other alkylalkynes 1m‐p, even bearing a
functional group (e.g., phenyl, Cl, ester), could all be
accommodated perfectly, albeit with lower yields (3ma‐pa).
Interestingly, two 2H‐azirine rings could be incorporated in the
resulting product 3qa when using 1,3‐diethynylbenzene 1q. Notably,
the synthetic utility of the annulation protocol in modified bioactive
molecules and drug derivatives were examined. Ethynylarenes built
on the backbones of menthol, glycine, D‐proline, adamantine, 3‐
oxo‐androstene and estrone10 underwent the annulation efficiently,
affording the valuable products 3ra‐wa in 55‐73% yields. However,
Scheme 2. Synthesis of 2H‐azirines.
optimization of the reaction conditions, the reaction in ClCH2CH2Cl
at 50 oC for 8 h afforded the desired azirine 3aa in 75% yield along
with trace of 1,2,5‐oxadiazole 2‐oxide 4aa (entry 1).9 Other solvents,
namely, THF, toluene, HCONMe2 and MeCONMe2 also exhibited
reactivity, but they were less effective than ClCH2CH2Cl (entries 2‐5).
A higher amount of TsNa (4 equiv) had no improvement of the yield
of 3aa (entry 6), and a lower amount of TsNa (2.2 equiv) had a
negative effect (entry 7). Brief screening of the amounts of t‐
BuONO indicated that 3 equiv was preferred (entries 1, 8 and 9).
Lowering (entry 10) or raising (entry 11) reaction temperatures led
to diminishing yields of 3aa. The diminishing yields in entry 10 & 11
was a result of incomplete conversion in lower temperatures and a
possibility of product 3aa instability under higher temperatures.
The reaction still proceeds efficiently at 1 mmol loading of alkyne 1a,
affording 3aa in high yield (entry 12).
Table 2
.
Synthesis of 2H‐azirines (3).
Table 1 Screening of optimal reaction conditionsa
N
N
N
Ts
Ts
Ts
Ts
Ts
Ts
N
Ts
R = H, 3ba, 78%
R = Me, 3ca, 75%
Ts R = MeO, 3da, 72%
R = Cl, 3ea, 58%
R = CN, 3fa, 68%
R = NO2, 3ga, 56%
3ha
, 63%
Ts
3ia, 57%
3ja, 72%
R
S
N
N
Ts
Ts
N
N
Ts
Ts
Ts
N
Ts
Ts
Entry Variation from the standard conditions Isolated yield (%)
75
Cl
O
Ts
Ph
Ts
Ts
Ts
3na, 33%
none
THF instead of ClCH2CH2Cl
toluene instead of ClCH2CH2Cl
HCONMe2 instead of ClCH2CH2Cl
MeCONMe2 instead of ClCH2CH2Cl
TsNa (4 equiv)
1
2
3ma, 57%
3oa, 32%
N
N
8
Ts
Ts
3ka
, 65%
O
3la, 41%
N
MeO
12
15
23
76
63
74
53
39
43
70
3
4
5
6
7
8
9
10 b
11
12c
N
Ts
Ts
Ts
O
Ts
Ts
3qa, 43%b
3pa, 40%
3ra, 55% (menthol derivative)
N
Ts
Ts
N
N
Ts
O
H
O
O
O
O
Ts
O
Ts
H
BocN
TsNa (2.2 equiv)
N
Boc
3ta, 73%
3sa, 69%
H
t‐BuONO (4 equiv)
t‐BuONO (2 equiv)
at 40 oC
N
3ua
Ts
, 63%
Ts
N
O
O
N
O
Ts
S
S
Ph
O
H
H
O
Ts
H
H
O
at 70 oC
none
Ph
H
H
O
O
3wa, 57% (estrone derivative)
3cb, 67%
3va, 58% (androstene derivative)
O
O
O
N
O
N
O
O
N
S
S
S
R2
a
S
S
Reaction conditions: 1a (0.2 mmol), 2a (3 equiv), t‐BuONO (3
O
S
O
N
O
O
O
R
S
S
o
b
S
R2
equiv), ClCH2CH2Cl (2 mL), 50 C, argon and 8 h. > 40% of 1a
was recovered. c 1a (1 mmol) and 16 h.
O
O
O
O
O
R
R
2 = Me, 3ch, 60%
R2 = c-propyl, 3ci, 43%
R2 = CH2CH2CO2Me, 3cj, 59%
S
R = p-Cl, 3cc, 41%
R = p-CN, 3cd, 30%
R = m-Me, 3ce, 51%
3cg, 56%
3cf, 61%
With the optimal reaction conditions in hand, we set out to
investigate the generality of the catalyst‐free tandem annulation
protocol with terminal alkynes 1 and sodium sulfinates 2 using t‐
BuONO as the nitrogen source for the synthesis of 2,2‐disulfonyl‐
a
Reaction conditions: 1 (0.2 mmol), 2 (3 equiv), t‐BuONO (3
o
b
equiv), ClCH2CH2Cl (2 mL), 50 C, argon and 8 h. 1a (1 mmol)
and 16 h. b 2a (6 equiv), t‐BuONO (6 equiv) and DCE (4 mL).
2 | J. Name., 2012, 00, 1-3
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ethyl propiolate (1x) had no reactivity for the reaction.
occurs and delivers the desired 2,2‐disulfonyl‐2H‐azirine 3.
View Article Online
DOI: 10.1039/C9CC00625G
In summary, we have developed a mild, catalyst‐free, chemo‐
This annulation technology was applicable a host of sodium
sulfinates (3cb‐cj), including arylsulfinates and alkylsulfinates. In the and site‐selective tandem annulation of various terminal alkynes
presence of alkyne 1c and t‐BuONO, the reaction could be with sodium sulfinates and t‐BuONO for producing 2,2‐disulfonyl‐
performed efficiently with sodium arylsulfinates containing various 2H‐azirines. This reaction allows the formation of four new chemical
aryl groups, such as C6H5 (3cb), p‐ClC6H4 (3cc), p‐CNC6H4 (3cd), m‐ bonds, two C(sp3)‐S bonds, one C(sp3)‐N bond and one C=N bond,
MeC6H4 (3ce), naphthalen‐2‐yl (3cf) and thiophen‐2‐yl (3cg). via radical‐mediated multiple‐functionalizations of terminal alkynes,
Alkysulfinates, possessing a methyl, a cyclopropyl or a 3‐methoxy‐3‐ and represents
oxopropyl group, were also competent reaction partners to access construction of the 2H‐azirine frameworks using tert‐butyl nitrite as
the corresponding products 3ch‐cj. the nitrogen source where avoids use of acid, base and transition‐
a new, straightforward technology for the
As shown in Scheme 3, control reaction of alkyne 1c with a metal catalysts. Moreover, additional highlights involves
mixture of TsNa 2a and sodium methanesulfinate (MsNa) 2h in the derivatization of the bioactive structural systems by incorporation
presence of t‐BuONO afforded three products, 3ca, 3ch and a cross of a 2,2‐disulfonyl‐2H‐azirine unit.
product 3cah (eqn (1)). The chemoselectivity supports addition of
We thank the National Natural Science Foundation of China
sulfonyl radical twice during the annulation process. Notably, the (Nos. 21801115, 21871126, and 21625203) and Jiangxi Educational
reaction of alkyne 1c with TsNa 2a and t‐BuONO was inhibited Committee Foundation of China (No. GJJ170612) for financial
completely by a radical inhibitor [e.g., TEMPO, 2,6‐di‐tert‐butyl‐4‐ support.
methylphenol (BHT) and hydroquinone], and 2,6‐di‐tert‐butyl‐4‐
(tosylmethyl)phenol 4 was formed by the reaction between BHT Notes and references
and TsNa (eqn (2)). These results suggest that the reaction is
initiated by sulfonyl radical.
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are proposed in Scheme 4 on the basis of the previous reported
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sulfinate 2 with t‐BuONO affords the sulfonyl radical, the NO radical
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sulfonyl radical across the C=C bond of the intermediate B gives the
C(sp3)‐centred radical intermediate C, which would sequentially
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O
R2
O
R2
O
R2
O
R2
O
NO
N
N
S
S
S
S
O
N
S
ON
R1
S
HO
N
S
O
O
O
O
O
O
O
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R1
R1
R1
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R1
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HNO2
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Scheme 4. Possible reaction mechanism
.
This journal is © The Royal Society of Chemistry 20xx
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