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GATE 2026 CY – Question 50

Organic Chemistry · Heterocyclic Compounds: Nomenclature of mono- and bicyclic, as well as mono- and di-heteroatomic compounds, Structure, preparation, properties and reactions of furan, pyrrole, thiophene, pyridine, indole, quinoline and isoquinoline. · 2 marks · Multiple select

The reaction(s) that produce(s) 2-methylindole as the major product is(are)

Four proposed routes to 2-methylindole.
  1. Option A in the figure
  2. Option B in the figure
  3. Option C in the figure
  4. Option D in the figure

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Show answer and explanation

Correct answer: (A) Option A in the figure; (B) Option B in the figure; (D) Option D in the figure

Explanation

A is reductive cyclization of the ortho-nitrobenzylidene acetone; B is Cadogan nitrene cyclization; D is a Gassman indole synthesis followed by desulfurization. C gives an indole-2-carboxylate rather than 2-methylindole.