• Amolak C Jain

      Articles written in Journal of Chemical Sciences

    • Synthesis of natural triisopentenylated flavanone, euchrenone a2

      Amolak C Jain Ashok K Prasad

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      Euchrenone a2 (7) isolated from the roots ofEuchresta japonica has been synthesised from 3-prenylphloroacetophenone (1) by other workers. We carried out its cyclodehydrogenation with dichloro dicyano quinone (DDQ) to obtain 6-acetyl-5,7-dihydroxy-2,2-dimethylchromene (2) which was ethoxymethylated in the 7-position to give 6-acetyl-7-ethoxymethoxy-5-hydroxychromene (3). Chalcone condensation of3 and 4-ethoxymethoxy-3-C-prenylbenzaldehyde (4) gave 4,6′-bisethoxymethoxy-2′-hydroxy-6″, 6″-dimethyl-3-C-prenylpyrano (2″, 3″–4,3) chalcone (5) which cyclised with methanolic sodium acetate to give protected 5,4′-bisethoxymethoxy-6″, 6″-dimethyl-3′-C-prenylpyrano (2″, 3″–7,8) flavanone (6). Deprotection of6 with 4% methanolic HCl yielded (7) with melting point and spectral data identical to that of the natural compound.

    • A study of ethoxymethylation in the 3-position of chroman-4-ones

      Amolak C Jain Rene Saksena

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      Ethoxymethylation of 7-hydroxy- (1) and 7-methoxy (6a) -chroman-4-ones with ethoxymethl chloride in the presence of anhydrous potassium carbonate and acetone results in formation of 3,3-bis-hydroxymethyl derivatives (3 and7) in very good yields, and not the expected 3-hydroxymethyl derivatives. But 5,7-dimethoxychroman-4-one (6b) does not react with ethoxymethyl chloride under the same conditions.

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