Novel sydnone derivatives carrying azidomethyl-1,2, 4-oxadiazole unit and their 1,3-dipolar cycloadditions

Abstract

A series of 1,2,4-oxadiazolymethyl sydnones carrying azido group were synthesized and subjected to react with a variety of alkenic and acetylenic dipolarophilic reagents; N-phenyl maleimide, phenyl vinyl sulfone, and phenyl propiolic acid. All the new products are identified by spectral/physical data including highresolution mass measurements and X-ray diffraction data.

Mesoionic compounds: the role of intermolecular interactions in their crystalline design

“…The search was narrowed to 23 structures. Crystallographic information files (CIFs) for compounds 1–24 are deposited at the Cambridge Crystallographic Data Centre (CCDC) under identification numbers and refcodes 987516 (YOMWAA) ( 1 ), 30 803243 (WADNOG) ( 2 ), 31 1028263 (JOMBUK) ( 3 ), 32 242317 (EWOXAP) ( 4 ), 33 722947 (SOLZOJ) ( 5 ), 34 1844074 (BIJKEN) ( 6 ), 35 1150485 (ETHBSD) ( 7 ), 36 889779 (XAZTOJ) ( 8 ), 37 1005653 (XAZJEQ) ( 9 ), 38 1298209 (XZBTZQ) ( 10 ), 39 1030491 (IJOWUB) ( 11 ), 40 1587204 (DEWYIQ) ( 12 ), 41 1972225 (TUFPIW) ( 13 ), 42 723513 (KUCYEN) ( 14 ), 43 2035296 (OVIWAU) ( 15 ), 14 2035298 (OVIWIC) ( 16 ), 14 2035297 (OVIWEY) ( 17 ), 14 784450 (MAGTEV) ( 19 ), 44 784451 (MAGTIZ) ( 20 ), 44 983378 (KIXHUW) ( 21 ), 45 983379 (KIXJAE) ( 22 ), 45 983380 (KIXJEI) ( 23 ), 45 and 983381 (KIXJIM) ( 24 ). 45 The compound 2,3-diphenyl-1,3,4-thiadiazolium-5-thiolate () ( 18 ) was synthesized according to the literature.…”

“…The search was narrowed to 23 structures. Crystallographic information files (CIFs) for compounds 1-24 are deposited at the Cambridge Crystallographic Data Centre (CCDC) under identification numbers and refcodes 987516 (YOMWAA) (1), 30 803243 (WADNOG) (2), 31 1028263 (JOMBUK) (3), 32 242317 (EWOXAP) (4), 33 722947 (SOLZOJ) (5), 34 1844074 (BIJKEN) (6), 35 1150485 (ETHBSD) (7), 36 889779 (XAZTOJ) (8), 37 1005653 (XAZJEQ) (9), 38 45 and 983381 (KIXJIM) (24). 45 The compound 2,3-diphenyl-1,3,4thiadiazolium-5-thiolate (1835915) (18) was synthesized according to the literature.…”

Controlled photorelease of alkynoic acids and their decarboxylative deprotection for copper-catalyzed azide/alkyne cycloaddition

“…Indeed, free 2alkynoic acids react with organic azides upon decarboxylation with similar regioselectivity to that of the corresponding terminal alkynes. [13][14][15][16][17] Heating or a metal, 18 typically Cu I , 17 catalysis is usually required for a successful decarboxylation. 19,20 The controlled release of molecules from photoremovable protecting groups (PPGs; caged groups) has the advantage in spatial and temporal delivery of a great variety of active reagents.…”