Efficient Routes to Acenaphthylene‐Fused Polycyclic Arenes/Heteroarenes and Heterocyclic Fluoranthene Analogues

Abstract

The acenaphthenone-derived α-oxoketene dithioacetal 2 has been subjected to various [3 + 3] aromatic and heteroaromatic annulation and other heterocyclization reactions previously developed in our laboratory, providing short and efficient routes to a diverse range of known and unknown acenaphtho-annulated linear and angular PAHs, heteroaromatics and five-membered heterocycles in good yields. Thus, benzo-and naphthoannulation of 2 with various allyl and benzyl Grignard reagents afforded substituted fluoranthenes 4a-c and benzo[k]fluoranthene 8, respectively, in good yields. Similarly, the parent benzo[j]fluoranthene 15a and its substituted derivative 16b have been synthesized by baseinduced conjugate 1,4-addition of arylacetonitriles to 2, followed by acid-induced cyclization of the conjugate adducts 12a-b to give 13a-b and subsequent further transformations. The adducts obtained by 1,4-addition of anions derived from acetophenone and acenaphthenone were subjected to heterocyclization in the presence of ammonium acetate to

Preparation and odor characteristics of nitriles derived from aldehydes

“…13 C NMR (75 MHz, CDCl 3 ): δ 23.6 (C2), 117.9 (C1), 127.9 (C3′ and 5′), 128.1 (C4′), 129.2 (C2′ and 6′), 129.9 (C1′). The NMR data matched with those reported in the literature 41 …”

Using Chou’s 5-Step Rule to Evaluate the Stability of Tautomers: Susceptibility of 2-[(Phenylimino)-methyl]-cyclohexane-1,3-diones to Tautomerization Based on the Calculated Gibbs Free Energies

“…Therefore, it was necessary to: (1) select or construct a valid benchmark dataset to train and test the predictor; (2) represent the samples with an effective formulation that truly reflects their intrinsic correlation with the target to be predicted; (3) introduce or develop a powerful algorithm to conduct the prediction; (4) properly perform cross-validation tests to objectively evaluate the anticipated prediction accuracy; and (5) establish a user-friendly web-server for the predictor that is accessible to the public. The advantages of this principle are: logic and transparency in action, the possibility for other researchers to repeat research, ease in developing methods and improving shortcomings, and, most importantly, convenience for use by other The substituent and naphthoannulation [57][58][59] are expected to affect the tautomeric preferences of these compounds [11][12][13]. Thus, 1 H and 13 C NMR experimental studies and quantum-chemical calculations were undertaken, to discover if some other (than those detected earlier) tautomers are stable enough to be present in solution.…”

“…Thus, 1 H and 13 C NMR experimental studies and quantum-chemical calculations were undertaken, to discover if some other (than those detected earlier) tautomers are stable enough to be present in solution. The substituent and naphthoannulation [57][58][59] are expected to affect the tautomeric preferences of these compounds [11][12][13]. Thus, 1 H and 13 C NMR experimental studies and quantum-chemical calculations were undertaken, to discover if some other (than those detected earlier) tautomers are stable enough to be present in solution.…”

“…Owing to the presence of the nitrogen atom and two carbonyl groups in their molecules, N-(2,2diacylvinyl)anilines are simply related to 1,2-dihydro-2,2-diacylmethylenequinolines, the enaminone tautomers of 2-(diacylmethyl)quinolines [53] (Figure 2). 2-(Anilinemethylidene)-cyclohexane-1,3-dione (Ea in Figure 3 The substituent and naphthoannulation [57][58][59] are expected to affect the tautomeric preferences of these compounds [11][12][13]. Thus, 1 H and 13 C NMR experimental studies and quantum-chemical calculations were undertaken, to discover if some other (than those detected earlier) tautomers are stable enough to be present in solution.…”

Synthesis of Benzo[k]fluoranthene Derivatives through Diels–Alder Reaction of 1,3‐Diarylbenzo[c]furans

“…H),6.25 (d, J = 7.2 Hz, 1 H),3.95 (s, 3 H), 2.89 (s, 3 H) ppm 13. C NMR (75 MHz, CDCl 3 ): δ = 159.4, 136.9, 136.5, 135.9, 135.6, 135.4, 134.9, 134.8, 134.7, 133.7, 133.4, 133.2, 133.1, 132.6, 131.3, 131.1, 130.1, 127.9, 127.9, 127.6, 127.1, 127.1, 126.9, 126.8, 126.1, 126.1, 125.9, 125.8, 125.8, 124.5, 122.3, 122.3, 114.8, 114.7, 55.5, 19.9 ppm.…”