<MultiModal>![N#CC1=C(OCCCC#N)C2=CC=CC=C2S1>$\mathrm{NaH}$(1.2equiv),dioxane,reflux>[$\mathbf{A}$],$\mathbf{A}$ is the reaction product](/media/uploads/2b54b118-8b78-4e6f-b5fa-ac611cac1559.png)</MultiModal>

Given that a new aromatic ring is formed in the reaction product $\mathbf{A}$, provide the structural formula of $\mathbf{A}$.
<MultiModal>![N#CC1=C(OCCCC#N)C2=CC=CC=C2S1>$\mathrm{NaH}$(1.2equiv),dioxane,reflux>[$\mathbf{A}$],$\mathbf{A}$是反应产物](/media/uploads/2b54b118-8b78-4e6f-b5fa-ac611cac1559.png)</MultiModal>

已知反应产物$\mathbf{A}$中形成了新的芳香环，试给出$\mathbf{A}$的结构式
All other options are incorrect
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<MultiModal>![NC1=C(C2C(C#N)SC3=CC=CC=C32)C=CO1](/media/uploads/48daa07c-f7da-495f-bc83-589051d44173.png)</MultiModal>
<MultiModal>![NC1=NC(OC=C2)=C2C3=C1SC4=CC=CC=C43](/media/uploads/379565ed-81a3-4953-a87a-d0419812c1d6.png)</MultiModal>
<MultiModal>![NC1=C2SC3=CC=CC=C3C2=C(C#N)CCO1](/media/uploads/8a836299-f3b7-4109-9720-e1ee764f76db.png)</MultiModal>
<MultiModal>![NC1=C2SC3=CC=CC=C3C2=CC=CO1](/media/uploads/c9d76537-2bef-492b-9672-0ae85dc72625.png)</MultiModal>
<MultiModal>![OC(C=C1)=C(N)C2=C1C3=CC=CC=C3S2](/media/uploads/cdf780c4-326e-4b60-81ea-633aea63333c.png)</MultiModal>
<MultiModal>![NC1=NC(OCC2)=C2C3=C1SC4=CC=CC=C43](/media/uploads/f522888c-e086-49c9-b7be-2ad1e63a7935.png)</MultiModal>
其他选项均不正确
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<MultiModal>![NC1=C2SC3=CC=CC=C3C2=C(C#N)CCO1](/media/uploads/8a836299-f3b7-4109-9720-e1ee764f76db.png)</MultiModal>
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<MultiModal>![OC(C=C1)=C(N)C2=C1C3=CC=CC=C3S2](/media/uploads/cdf780c4-326e-4b60-81ea-633aea63333c.png)</MultiModal>
<MultiModal>![NC1=NC(OCC2)=C2C3=C1SC4=CC=CC=C43](/media/uploads/f522888c-e086-49c9-b7be-2ad1e63a7935.png)</MultiModal>
Based on the prompt, a new aromatic ring is formed in the reaction product $\mathbf{A}$, excluding options B, E, and F.

First, the substrate is deprotonated by $\mathrm{NaH}$ at the position adjacent to the cyano group, yielding intermediate $\mathbf{1}$.

<MultiModal>![Intermediate $\mathbf{1}$: N#CC1=C(OCC[CH-]C#N)C2=CC=CC=C2S1](/media/uploads/15f40fde-2462-4969-8ed1-e72c79b46318.png)</MultiModal>

<Checkpoint>[Intermediate $\mathbf{1}$: N#CC1=C(OCC[CH-]C#N)C2=CC=CC=C2S1](1)</Checkpoint>

Then, the formed carbanion undergoes Michael addition to the $\alpha$-$\beta$ unsaturated system to obtain intermediate $\mathbf{2}$.

<MultiModal>![Intermediate $\mathbf{2}$: N#C[C-]1SC2=CC=CC=C2C13OCCC3C#N](/media/uploads/12b2e9cb-76b0-49c3-ac75-90633e150067.png)</MultiModal>

<Checkpoint>[Intermediate $\mathbf{2}$: N#C[C-]1SC2=CC=CC=C2C13OCCC3C#N](1)</Checkpoint>

Then, rearomatization occurs, and the oxyanion departs, yielding intermediate $\mathbf{3}$.

<MultiModal>![Intermediate $\mathbf{3}$: [O-]CCC(C1=C(C#N)SC2=CC=CC=C21)C#N](/media/uploads/4c09489c-0615-4149-a305-7faf61ec839f.png)</MultiModal>

<Checkpoint>[Intermediate $\mathbf{3}$: [O-]CCC(C1=C(C#N)SC2=CC=CC=C21)C#N](1)</Checkpoint>

The oxyanion attacks the cyano group to form a ring, yielding intermediate $\mathbf{4}$.

<MultiModal>![Intermediate $\mathbf{4}$: [N-]=C1C(C2=C(C#N)SC3=CC=CC=C32)CCO1](/media/uploads/064ce098-b88f-4b57-a1f2-e08244724ad3.png)</MultiModal>

<Checkpoint>[Intermediate $\mathbf{4}$: [N-]=C1C(C2=C(C#N)SC3=CC=CC=C32)CCO1](1)</Checkpoint>

The imine anion further attacks the cyano group to form a ring, yielding intermediate $\mathbf{5}$.

<MultiModal>![Intermediate $\mathbf{5}$: [N-]=C1C2=C(C3CCOC3=N1)C4=CC=CC=C4S2](/media/uploads/22623311-5251-4383-8048-3013388b7732.png)</MultiModal>

<Checkpoint>[Intermediate $\mathbf{5}$: [N-]=C1C2=C(C3CCOC3=N1)C4=CC=CC=C4S2](1)</Checkpoint>

Since the imine is unstable, and according to the prompt, a new aromatic ring is formed in the reaction product $\mathbf{A}$, intermediate $\mathbf{5}$ further aromatizes to obtain product $\mathbf{A}$.

<MultiModal>![Product $\mathbf{A}$: NC1=NC(OCC2)=C2C3=C1SC4=CC=CC=C43](/media/uploads/f522888c-e086-49c9-b7be-2ad1e63a7935.png)</MultiModal>
根据提示，反应产物$\mathbf{A}$中形成了新的芳香环，排除选项B、E、F

首先，底物被$\mathrm{NaH}$夺去氰基邻位的质子得到中间体$\mathbf{1}$

<MultiModal>![中间体$\mathbf{1}$：N#CC1=C(OCC[CH-]C#N)C2=CC=CC=C2S1](/media/uploads/15f40fde-2462-4969-8ed1-e72c79b46318.png)</MultiModal>

<Checkpoint>[中间体$\mathbf{1}$：N#CC1=C(OCC[CH-]C#N)C2=CC=CC=C2S1](1)</Checkpoint>

接着形成的碳负离子对$\alpha$-$\beta$不饱和体系进行micheal加成得到中间体$\mathbf{2}$

<MultiModal>![中间体$\mathbf{2}$：N#C[C-]1SC2=CC=CC=C2C13OCCC3C#N](/media/uploads/12b2e9cb-76b0-49c3-ac75-90633e150067.png)</MultiModal>

<Checkpoint>[中间体$\mathbf{2}$：N#C[C-]1SC2=CC=CC=C2C13OCCC3C#N](1)</Checkpoint>

接着重新芳构化，氧负离子离去，得到中间体$\mathbf{3}$

<MultiModal>![中间体$\mathbf{3}$：[O-]CCC(C1=C(C#N)SC2=CC=CC=C21)C#N](/media/uploads/4c09489c-0615-4149-a305-7faf61ec839f.png)</MultiModal>

<Checkpoint>[中间体$\mathbf{3}$：[O-]CCC(C1=C(C#N)SC2=CC=CC=C21)C#N](1)</Checkpoint>

氧负离子进攻氰基成环，得到中间体$\mathbf{4}$

<MultiModal>![中间体$\mathbf{4}$：[N-]=C1C(C2=C(C#N)SC3=CC=CC=C32)CCO1](/media/uploads/064ce098-b88f-4b57-a1f2-e08244724ad3.png)</MultiModal>

<Checkpoint>[中间体$\mathbf{4}$：[N-]=C1C(C2=C(C#N)SC3=CC=CC=C32)CCO1](1)</Checkpoint>

亚胺负离子进一步进攻氰基成环，得到中间体$\mathbf{5}$

<MultiModal>![中间体$\mathbf{5}$：[N-]=C1C2=C(C3CCOC3=N1)C4=CC=CC=C4S2](/media/uploads/22623311-5251-4383-8048-3013388b7732.png)</MultiModal>

<Checkpoint>[中间体$\mathbf{5}$：[N-]=C1C2=C(C3CCOC3=N1)C4=CC=CC=C4S2](1)</Checkpoint>

由于亚胺不稳定，且根据题干提示反应产物$\mathbf{A}$中形成了新的芳香环，因此中间体$\mathbf{5}$进一步芳构化得到产物$\mathbf{A}$

<MultiModal>![产物$\mathbf{A}$：NC1=NC(OCC2)=C2C3=C1SC4=CC=CC=C43](/media/uploads/f522888c-e086-49c9-b7be-2ad1e63a7935.png)</MultiModal>