One-Pot Construction of Diverse Products using Versatile Cyclopropenones

Article abstract of DOI:10.1002/adsc.202100845

Tunable C?H activation cascade reactions between quinazolinones and cyclopropenones have been developed. Notably, cyclopropenones, acting as multi-functional building blocks, could be assembled to construct up to 10 distinct heterocyclic scaffolds in a one-pot manner. (Figure presented.).

Full text of DOI:10.1002/adsc.202100845

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doi.org/10.1002/adsc.202100845
One-Pot Construction of Diverse Products using Versatile
Cyclopropenones
Tianle Huang,+a Chunyan Yang,+a Yuesen Shi,a Jian Chen,a Ting Wang,a
Xiaoyu Guo,a Xuexin Liu,a Haosheng Ding,a Zhouping Wu,a Li Hai,a,* and
Yong Wua,*
a
Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of
Pharmacy, Sichuan University, Chengdu 610041, People’s Republic of China
E-mail: wyong@scu.edu.cn; smile@scu.edu.cn
+
These authors contributed equally.
Manuscript received: July 7, 2021; Revised manuscript received: August 31, 2021;
Version of record online: ■■■, ■■■■
Supporting information for this article is available on the WWW under https://doi.org/10.1002/adsc.202100845
CÀ H activation (Figure 1A).[5] Notably, The CÀ H
Abstract: Tunable CÀ H activation cascade reac-
functionalization cascade has emerged as a powerful
tions between quinazolinones and cyclopropenones
strategy to construct complex molecules starting from
have been developed. Notably, cyclopropenones,
acting as multi-functional building blocks, could be
limited feedstocks.[6] However, its potential in scaffold
diversity synthesis remains underexplored, largely due
assembled to construct up to 10 distinct heterocyclic
to the difficulty in precisely controlling the degree and
scaffolds in a one-pot manner.
selectivity of reaction cascades that involve cleavage
and construction of multiple chemical bonds.
We hence hoped to develop a tunable CÀ H
activation cascade strategy to realize diversity syn-
thesis using as few substrates as possible in a one-pot
manner. As shown in Figure 1, we envisioned that this
goal could be achieved by using a versatile coupling
Keywords: One-pot construction; CÀ H activation;
Cascade protocol; Quinazolinone; Cyclopropenone
Small molecules with structural complexity and diver- reagent. A few prerequisites must be fulfilled con-
sity play a crucial role in the fields of drug discovery currently for a proof of concept: 1) the coupling
and chemical biology research.[1] The quest for partner is feasible for further transformations and rapid
efficient strategies that provide facile access to new, participation in subsequent CÀ H activation processes
complex, and diverse molecules continues to be an (Figure 1B); 2) Multiple CÀ H bonds can be activated
important and stimulating thrust to academic and continuously in a controllable manner (Figure 1C); 3)
industrial research.[2] In the past decades, diversity- the functionalization sequences of multiple coupling
oriented synthesis (DOS) has imparted a paradigm partners are tunable (Figure 1D). Notably, we proposed
shift in the construction of structurally diverse molec- to finely tune all above-mentioned approaches by
ular libraries.[3] However, a consensus has emerged solely manipulating reaction conditions, including
that DOS strategy usually demands multiple reaction catalysts, substrate ratio, solvent, etc. The aforemen-
steps and diverse substrates. The efficient creation of tioned maneuvers have not fully been developed, so it
diverse molecules with limited substrates in a one-pot is rather challenging to fully integrate them to make
manner remains a formidable challenge.
more progress in diversity by precisely controllable
Featuring step- and atom-economy, transition metal conditions. For example, in fact, the first step of CÀ H
(TM)-catalyzed CÀ H functionalization represents an bond functionalization may lead to significant changes
appealing strategy to construct molecules, dramatically in steric and electronic properties of the substrate,
reshaping the logic of synthetic chemistry.[4] Directing which hampers the efficiency of the succedent CÀ H
groups (DGs) that direct metal catalysts close to target bond functionalization. In addition, it is often incom-
CÀ H bonds, facilitating selective bond cleavage and patible for multiple reaction conditions involved in the
functionalization processes have been widely used in continuous introduction of different groups.
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Figure 1. Diversity synthesis design via CÀ H functionalization.
Known as a highly efficient coupling reagent,
cyclopropenone has been widely used in the field of
CÀ H activation.[7] It could be used as a versatile
substrate in the construction of different scaffolds.[8] In
our previous work, we successfully realized a diver-
gent synthesis strategy to obtain three kind of
compounds between cyclopropenones and N-
nitrosoanilines.[9] Quinazolinones have exhibited a
wide range of biological activities[10] and have been
used as an excellent DG.[11] Herein, we hoped to
explore the CÀ H activation reactions of cycloprope-
nones and quinazolinones to realize the above designs.
We initially selected 2-phenylquinazolin-4-(3H)-
one 1a and diphenylcyclopropenone 2a as model
substrates and ran the reaction in the presence of
different catalysts, Ag salts, additives, oxidants, and
solvents. To our delight, a tertiary indenol product 3a
was obtained in 85% yield in the presence of
°
[RhCp*Cl2]2 and AgSbF6 in DCM at 100 C under air
(Figure 2B) (for a comprehensive investigation of the
conditions, see SI). Indenols are an important class of
organic compounds known for several important bio-
logical activities such as antibacterial and insecticidal
properties (Figure 2A).[12] Thus, the synthesis of inden-
ols also attracted the attention of chemical workers.[13]
We investigated the substrate scope and limitations for
Figure 2. Examples, substrate scope and mechanism.
the indenol product synthesis (Figure 2B). The C6 or with 2a to afford corresponding products 3e–3m in
C7-(OMe, Me, Cl)-substituted 2-phenylquinazolin-4- 71–87% yields. No obvious steric or electronic effect
ones treated with 2a gave quinazolinone derivatives was observed. It’s worth noting that multi-substituted
3b–3d in good yields. Quinazolinones bearing various substrates and 2-(naphthalen-1-yl)quinazolinone could
substitutions on the 2-phenyl ring such as 4-tBu, 4-F, also furnish the targeted molecules in good yields
4-Br, 4-CF3, 3-OCF3, and 2-OMe reacted effectively under the standard conditions (3n–3p). Substituted
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cyclopropenone was also proved to be good material
for this transformation (3q).
Plausible mechanism was proposed to reveal how
the product 3a was synthesized, based on the corre-
sponding mechanism experiments (see SI for details)
and the reported CÀ H activation works (Fig-
ure 2C).[11e,14] Initial anion exchange affords the active
[RhCp*X2] species, which might involve the coordina-
tion of the nitrogen atom of 1a to the metal centre.
Followed by displacement of aromatic CÀ H bond, the
five-membered metal-cycle A would be achieved.
Intermolecular oxidative addition by cyclopropenone
then generates the cyclobutanone Rh(V) intermediate
C. Subsequent reductive elimination generates C-
(benzyl)À C(carbonyl) bond in the intermediate D. E
will be achieved rapidly by the second CÀ H activation
Figure 3. Transformation of cyclopropenone and reactions.
through the 1,3-migration of the Rh catalyst from the 7 were smoothly produced in moderate yield by further
vinyl to aryl. Finally, the product 3a is generated reaction between the intermediate 3a and diphenylace-
through the intramolecular nucleophilic attack and tylene generated from 2a (Figure 4). Interestingly, 3a
protonation, while releasing the active catalyst for the underwent a Rh-catalyzed CÀ H olefination/cyclization
next catalytic cycle.
process while its indenol moiety proceeded a ring-
Besides, diphenylcyclopropenone could efficiently opening process to form a chalcone side chain at a
°
convert into diphenylacetylene when exposed to high temperature (120 C). The structure of product 6d
ultraviolet.[15] Indisputably, the preparation of symmet- was unambiguously confirmed by the single crystal X-
ric and asymmetric arylacetylene compounds remains ray diffraction analysis (Figure 4, 6d). At a relatively
°
to be tedious. Diarylacetylene compounds are usually low temperature (70 C), the succeeding steps could
synthesized from aldehydes and compounds with not take place, which may be due to unfavourable
active hydrogen by bromination and debromination.[16] steric factors. Consequently, an alternative pathway is
They can also be obtained by metal-catalyzed coupling followed. The meta CÀ H bond of intermediate 3a was
methods, which inevitably require the use of halogen- activated to further afford a naphthalene ring product
ated compounds.[17] Because of above difficulties,
decarbonylation of cyclopropenones under high-tem-
perature pyrolysis, photolysis or in the presence of
certain catalysts (such as [Rh(COD)Cl]2) has become
an important synthesis strategy for symmetrically or
asymmetrically substituted alkynes.[18] Thus directly
using cyclopropenones as the precursor of alkynes to
participate in the CÀ H olefination/cyclization reaction
in a one-pot manner is a desired cost-effective process.
Here we successfully synthesized a fused tetracyclic
heteroarene 4a, which was reported in our recent
work, by CÀ H olefination/cyclization cascade between
1a and 2a under the ultraviolet without any photo-
catalysts (Figure 3). We also found that the cyclo-
propenone can be transformed into 2-phenylacetophe-
none efficiently under the catalysis of 5 mol% K2CO3.
2-Phenylacetophenone generated from 2a could be
used as a benzoyl radical donor to react with 1a co-
catalyzed by Cu(OAc)2 (5 mol%) and Pd(OAc)2
(5 mol%), affording the product 5a (Figure 3). A wide
range of quinazolinones and cyclopropenones could be
well tolerated under the standard conditions to synthe-
size product 4 and 5 (see SI for details).
To achieve the goal mentioned before, we further
attempted to realize diversity synthesis by one-pot
sequential unsymmetrical twofold CÀ H functionaliza-
Figure 4. Scope for synthesis of product 6 and 7.
tion. Just as designed, the diverse new products 6 and
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7a. When 1.0 equiv. of NaOAc was used as the
additive, the yield of 7a was further improved. More-
over, product 8a was obtained by a further Pd-
catalyzed coupling of the double bond of chalcone
moiety with the CÀ H bond of the benzene ring
(Figure 4).
Subsequently, we tried to tune the sequence of
cascade reactions. Gratifyingly, the product 4a was
proved to be an effective intermediate in the following
exploration. Through controlling the introduction
sequences of diverse functional groups, modules of
cascade reactions could be flexibly assembled like
Lego, generating more different scaffolds (products
9a–12a) (Figure 4). At first, cyclopropenone 2a was
added to the reaction solution containing 4a, and
compound 9a was attempted to obtain under the
catalysis of [RhCp*(OAc)2]2. As expected, compound
9a was successfully produced at room temperature in
considerable yield. Next, the product 10a was also
smoothly obtained by a further Pd-catalyzed coupling
of the double bond of chalcone moiety with the CÀ H
bond of the benzene ring. In the presence of [Ru(p-
cymene)Cl2]2, compound 11a was formed by an
unprecedented sequential CÀ H functionalization on 3-
and 2-positions of the benzene ring. The unusual
structures of product 11 were confirmed by a single
crystal X-ray diffraction analysis of 11c. Finally,
compound 12a was also successfully obtained by
further reaction of the 2-phenylacetophenone trans-
formed from 2a with the intermediate 4a.
We surveyed the scope and limitation of substrates
for the synthesis of product 6–12. As summarized in
Figure 4 and Figure 5, quinazolinones 1 or cyclo-
propenones 2 substituted with different functional
groups at different positions could proceed smoothly
under optimal conditions of different reactions, provid-
ing the corresponding products in moderate to good
yields. Finally, we investigated the mechanism of these
reactions, and the possible pathways were proposed in
the SI.
In summary, we designed and developed a series of
CÀ H activation reactions which enable direct access to
up to 10 heterocyclic scaffolds using cyclopropenone
as a multifunctional coupling reagent. The good regio-/
chemoselectivity and wide substrate scope for both
quinazolinones and cyclopropenones demonstrated the
applicability of these reactions. We also investigated
and proposed the corresponding mechanism of these
reactions. This work highlights the tremendous poten-
tial of tunable cascade reactions to deliver compound
libraries enriched in structural diversity from versatile
substrates. Meanwhile, this one-pot divergent synthesis
strategy starting from limited starting materials would
provide insights for the improvement of DOS.
Figure 5. Scope for synthesis of product 9, 10, 11 and 12.
Experimental Section
General procedure for the synthesis of compound 3 (3a as an
example).
Quinazolinone 1a (0.10 mmol), diphenylcyclopropenone 2a
(0.105 mmol), [RhCp*Cl2]2 (0.05 mmol), AgSbF6 (0.3 mmol)
were charged into a pressure tube, to which was added DCM
°
(2.0 mL) under air. The reaction mixture was stirred at 100 C
for 36 h. After completion of the reaction (monitored by TLC),
the reaction mixture was cooled to room temperature and the
solvent was removed under reduced pressure. The residue was
purified by silica gel chromatography using PE/EA (about
20/1~2/1) to afford compound 3a as a white solid.
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CCDC-2012594 and 2012595 contain the supplementary
crystallographic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic Data
Centre via www.ccdc.cam.ac.uk/data_request/cif.
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Acknowledgements
We are grateful for financial support from the National NSF of
China (grant number 81573259 and 81874291).
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One-Pot Construction of Diverse Products using Versatile Cy-
clopropenones
Adv. Synth. Catal. 2021, 363, 1–7
T. Huang, C. Yang, Y. Shi, J. Chen, T. Wang, X. Guo, X. Liu,
H. Ding, Z. Wu, L. Hai*, Y. Wu*