Advances in Heterocyclic Chemistry, Vol. 39 by Alan R. Katritzky

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By Alan R. Katritzky

Meant for natural chemists, this quantity follows the layout of earlier volumes and gives updated info on chosen parts of heterocyclic chemistry.

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Guerret-Rigail, and R. Jacquier, Bull. Soc. Chim. , 1994 (1972). 52 [Sec. 1 JAMES G. KEAY I. 159However, a different orientation of the same substituents leads to the ring-opened product 311, with cleavage occurring between C-2 and N-3 when LAH is used. 159,162- 164 The position and nature of the substituents has been shown to affect the reaction markedly; for instance, NBH and LAH both generate 2-phenyl-3methyl- 1,2-dihydro-4-quinazolinone (314) from the parent heterocycle 313. This compound may then be converted to the ring-cleaved product 315 on further heating with NBH in ethanol.

Haidukewych and A. 1. ,3031 (1972). , Fr. Demande 2,187,761 (1974) [CA 81, 13101f(1974)]. G . M. Clarke and P. Sykes, J. C. Chem. , 370 (1965). G . M. Clarke and P. Sykes, J. C. 141 1 (1967). Sec. 124 \s’ c, H*O S ‘’ RWC 0 $a, b i N. D. Bachi, J. C. S. Perkin I , 310 (1972). 126 12’ D. S u c k J. Prakt. Chem. 314,961 (1972). -L. -C. Roze, and G . Duguay, J. Chem. , 72 (1982). KEAY [Sec. A in such systems. Iz7This the imine bond in 2-phenyl-6H-l,3-thiazines results partially from the bond polarization effects of the phenyl group and partially from protonation.

R. Musgrave, and P. Urben, J. C. Perkin I, 2584 (1974). L. S. Besford, G . Allen, and J. M. Bruce, J. Chem. , 2867 (1 963). J. Daunis, M. Guerret-Rigail, and R. Jacquier, Bull. Soc. Chim. , 1994 (1972). 52 [Sec. 1 JAMES G. KEAY I. 159However, a different orientation of the same substituents leads to the ring-opened product 311, with cleavage occurring between C-2 and N-3 when LAH is used. 159,162- 164 The position and nature of the substituents has been shown to affect the reaction markedly; for instance, NBH and LAH both generate 2-phenyl-3methyl- 1,2-dihydro-4-quinazolinone (314) from the parent heterocycle 313.

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