Methylenation of the nitrogen–halogen bond of positive halogen compounds

Abstract

The N-X bond of positive halogen compounds (I) can be readily methylenated at 15" with diazomethane to give the N-halogenomethyl derivatives (111). not isolated as such but directly condensed with nucleophiles [sodium pnitrophenoxide, diethyl phthalimido(sodio)malonate, and morpholine] ; the parent N-H compounds (VII) are formed as secondary products. This new reaction has been applied to N-halogeno-N-substituted carboxamides, sulphonamides, phosphoramides, and urethanes. The mechanism of the methylene insertion into the N-X linkage Nacional de La Plata, La Plata, Argentina is discussed.

N‐Sulfonyl‐1,2,3,4‐tetrahydroisoquinoline Derivatives: Synthesis, Antimicrobial Evaluations, and Theoretical Insights

“…The yields were calculated from purified compounds. The synthetized products were identified by comparing physical data previously reported [30–32] . Melting points were determined in sealed capillary tubes and were uncorrected.…”

“…The reactants, specifically N ‐phenyl‐ethylsulfonamide ( 1 ), trioxane, and PWMo, were employed in quantities of 1 mmol, 3 mmol, and 1 % mmol, respectively. The N ‐phenyl‐ethylsulfonamide ( 1 ) was obtained from a previous study [30] …”

Hydantoins: Synthesis, properties and anticonvulsant activity

“…Mono-N-supstituisani derivati se mogu dobiti alkilovanjem na N-1 u specijalnim uslovima, npr. uz natrijum-hidrid u dimetilformamidu [19].…”

Mass spectra of heterocyclic compounds. II‐Hexahydro‐1,3,5,‐triazines

“…186* 214(8); 122(10); 76(9); 57 (21) (6); 28(12); 18 (7) 214 76(8); 64(6); 57(12); 56(11) (9) 162(11); 99(13); 98(12); 84 (7); 70(20); 69(16); 57(25); 56(8); 55(10); 43(90); 41(25) 126 (6); 77(6); 73(11); 44 (7) 338 119 (7); 118(9); 65(14) (0.4) 338 65(13) (5) 378 75(16) (8) 400 625(9); 106(9); 92(19); 82 (9) (6); 76(28); 75(21); 64(11); 400 198(9); 156(10); 138(6); 106 (3) (6); 92(23); 76(38); 75(46); 50(10) 74(8); 65(8); 64(9); 63 (7); SO(28); 39 (6) 426 650(8); 196(33); 120(9); 104 (3) (28); 103(22); 82 (6); 77(13); 76(15); 75(8); 50 (7) a For compounds 4 and 13 see Fig. 1 and Table 2…”