1-(Phenyl-sulfon-yl)-1H-indole-2-carbaldehyde.

The title compound, C15H11NO3S, was prepared by a facile synthetic approach. The N atom in the pyrrole ring of the indole moiety is pyramidal (bond-angle sum = 350.0°) and the phenyl ring of the phenyl-sulfonyl motif forms a dihedral angle of 76.24 (7)° with the mean plane of the indole ring system. In the crystal, C-H⋯O and C-H⋯π inter-actions link the mol-ecules into a three-dimensional network.

Crystal structures and biological activity of 1,1,4-triphenyl-substituted 1,3-enyne compounds.

1,3-Enyne structural motifs are versatile building blocks in organic synthesis and occur widely in various natural products with many of them being highly active as cytotoxic macrolides and antitumour antibiotics. This article presents the crystal structure of three 1,1,4-triphenyl-substituted 1,3-enynes, viz. 4-(2-methylphenyl)-1,1-diphenylbut-1-en-3-yne, C23H18 (1), 4-(2-methoxyphenyl)-1,1-diphenylbut-1-en-3-yne, C23H18O (2), and 4-(4-nitrophenyl)-1,1-diphenylbut-1-en-3-yne, C22H15NO2 (3). The benzene ring at position 4 of the but-1-en-3-yne group bears a weakly activating methyl group in compound 1, a moderately activating methoxy group in 2 and a strongly deactivating nitro group in 3. The crystal structures of 1 and 3 both have monoclinic symmetry, while that of 2 is orthorhombic, and all of them have one molecule in the asymmetric unit. All three compounds were investigated for their antibacterial and antifungal activities. Interestingly, enyne 2 is the only compound tested that inhibited the growth of Aspergillus niger.

Palladium-Catalyzed One-Pot Conversion of Aldehydes and Ketones into 4-Substituted Homopropargyl Alcohols and 5-En-3-yn-1-ols †.

Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generated the equivalent of 1,3-dilithiopropyne, which adds regiospecifically to aldehydes and ketones to produce homopropargyl alcohols. The lithium acetylide intermediate formed in this protocol can be further reacted with aromatic and vinyl halides, under palladium catalysis, to produce 4-substituted homopropargyl alcohols and 5-en-3-yn-1-ols, respectively, in one-pot with good overall yields.

A new method for the preparation of 1,5-diynes. Synthesis of (4E,6Z,10Z)-4,6,10-hexadecatrien-1-ol, the pheromone component of the cocoa pod borer moth Conopomorpha cramerella.

[reaction: see text] A new method for the synthesis of 1,5-diynes, from the reaction of 1,3-dilithiopropyne and propargyl chlorides, was developed. This new methodology was used to prepare (4E,6Z,10Z)-4,6,10-hexadecatrien-1-ol, one of the pheromone components of the cocoa pod borer moth Conopomorpha cramerella, in 51% overall yield.