854:
784:
326:
233:
759:
49:
965:
803:
39:
26:
949:
918:
535:
853:
797:
are both variations on the
BischlerâNapieralski reaction. A PictetâGams reaction works similarly to the BischlerâNapieralski reaction; the only difference being that an additional hydroxy group in the reactant provides a site for dehydration under the same reaction conditions as the cyclization to
724:
of the acid sulfate. Weissgerber developed a more rapid route in 1914 by selective extraction of coal tar, exploiting the fact that isoquinoline is more basic than quinoline. Isoquinoline can then be isolated from the mixture by fractional crystallization of the acid sulfate.
783:
1243:(Collection of Work in Chemistry in the Netherlands), vol.4, no. 4, pages 125â129. See also: S. Hoogewerf and W.A. van Dorp (1886) "Sur quelques dĂ©rivĂ©s de l'isoquinolĂ©ine" (On some derivatives of isoquinoline),
1426:
548:
779:. The resulting 1-substituted 3,4-dihydroisoquinoline can then be dehydrogenated using palladium. The following BischlerâNapieralski reaction produces papaverine.
375:
1399:
580:- as well as the name of a family of many thousands of natural plant alkaloids, any one of which might be referred to as "an isoquinoline". It is a
728:
Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. The
721:
1030:
derivatives have been found to have the same neurochemical properties as MPTP. These derivatives may act as precursors to active neurotoxins.
1373:
1130:
768:
1301:
1270:
639:. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes in form of platelets that have a low
340:
1293:
1262:
977:
1217:
Nagatsu, T. "Isoquinoline neurotoxins in the brain and
Parkinson's disease" Neuroscience Research (1997) volume 29, pp. 99â111.
870:
1421:
758:
729:
48:
1059:
794:
283:
38:
866:
304:
130:
972:
platinum complexes of urea functionalized isoquinolines have been used as anion receptors for chloride and sulfate.
1114:
829:
679:
555:
478:
1022:), the precursor to MPP, was found and linked to Parkinson's disease in the 1980s. The active neurotoxins destroy
802:
240:
790:
862:
836:
798:
give the isoquinoline rather than requiring a separate reaction to convert a dihydroisoquinoline intermediate.
508:
228:
1416:
1027:
1007:
964:
817:
1287:
821:
170:
1239:
S. Hoogewerf and W.A. van Dorp (1885) "Sur un isomére de la quinoléine" (On an isomer of quinoline),
776:
605:
68:
1111:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1023:
874:
772:
321:
96:
1019:
671:
1319:"MetalâOrganic Anion Receptors: Arranging Urea Hydrogen-Bond Donors to Encapsulate Sulfate Ions"
1369:
1338:
1297:
1266:
1126:
581:
1361:
1356:
Niwa, Toshimitsu; Kajita, Mitsuharu; Nagatsu, Toshiharu (1998). "Isoquinoline
Derivatives".
1330:
1118:
941:
809:
675:
656:
577:
398:
292:
764:
Several other methods are useful for the preparation of various isoquinoline derivatives.
660:
636:
600:
ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline
190:
1393:
106:
325:
232:
150:
732:
provides an efficient method for the preparation of isoquinoline. This reaction uses a
601:
526:
25:
1410:
910:
882:
652:
589:
468:
458:
221:
948:
1047:
987:
930:
733:
571:
1182:
Quinoline-Reds" Journal of the
Chemical Society (1922) volume 121, pp. 1029â1033.
754:
can be used, to produce the same result using the
Schlittler-MĂŒller modification.
272:
1365:
1122:
1089:
1011:
744:
693:
632:
771:
an ÎČ-phenylethylamine is acylated and cyclodehydrated by a Lewis acid, such as
1289:
Name
Reactions: A Collection of Detailed Mechanisms and Synthetic Applications
1259:
Name
Reactions: A Collection of Detailed Mechanisms and Synthetic Applications
1206:
Comprehensive
Heterocyclic Chemistry II: A Review of the Literature 1982â1995
957:
937:
825:
701:
640:
617:
613:
423:
181:
1342:
1318:
1010:, a slowly progressing movement disorder, is thought to be caused by certain
1083:
1071:
1051:
926:
847:
616:. The isoquinoline ring in these natural compound derives from the aromatic
609:
585:
917:
1067:
813:
717:
620:
597:
574:
201:
1317:
Bondy, Chantelle R.; Gale, Philip A.; Loeb, Stephen J. (28 April 2004).
986:
Bisbenzylisoquinolinium compounds are compounds similar in structure to
839:
210:
1055:
748:
740:
648:
644:
593:
444:
259:
241:
1334:
976:
991:
843:
751:
697:
161:
525:
Except where otherwise noted, data are given for materials in their
635:
liquid at temperatures above its melting point with a penetrating,
1063:
1043:
995:
975:
886:
689:
141:
129:
119:
1392:
1015:
737:
664:
897:
Intramolecular aza Wittig reactions also afford isoquinolines.
1039:
1204:
Katritsky, A.R.; Rees, C.W.; Scriven, E.F. (Eds.). (1996).
852:
309:
47:
37:
1026:, leading to parkinsonism and Parkinson's disease. Several
1286:
Li, J. J. (2014). "Schlittler–MĂŒller modification".
816:
forms an imine, which undergoes a cyclization to form a
439:
Colorless oily liquid; hygroscopic platelets when solid
1403:. Vol. 22 (11th ed.). 1911. pp. 758â759.
1150:
Determination of
Organic Structures by Physical Methods
990:. They have two isoquinolinium structures, linked by a
720:
in 1885 by Hoogewerf and van Dorp. They isolated it by
608:
is the structural backbone in many naturally occurring
543:
1148:
Brown, H.C., et al., in Baude, E.A. and Nachod, F.C.,
808:
In a PictetâSpengler reaction, a condensation of a ÎČ-
1257:Li, J. J. (2014). "Pomeranz–Fritz reaction".
736:and aminoacetoaldehyde diethyl acetal, which in an
933:(all derived from 1,2,3,4-tetrahydroisoquinoline).
905:Isoquinolines find many applications, including:
857:1,2,3,4-Tetrahidroisoquinolines biosynthesis: in
271:
105:
1165:(3rd ed.). Essex, UK: Addison Wesley Longman.
463:26â28 °C (79â82 °F; 299â301 K)
349:InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
1038:Isoquinolines are used in the manufacture of
359:InChI=1/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
8:
1230:(13th ed.). Whitehouse Station, NJ: Merck.
1191:Katritsky, A.R.; Pozharskii, A.F. (2000).
743:react to form isoquinoline. Alternatively,
1245:Recueil des Travaux Chemiques des Pays-Bas
1241:Recueil des Travaux Chemiques des Pays-Bas
324:
231:
189:
17:
1427:Substances discovered in the 19th century
850:a biological Pictect-Spengler synthesis:
291:
1323:Journal of the American Chemical Society
1102:
570:is an individual chemical specimen - a
380:
345:
320:
209:
1358:Pharmacology of Endogenous Neurotoxins
1226:O'Neil, Maryadele J. (Ed.). (2001).
473:242 °C (468 °F; 515 K)
222:
1144:
1142:
1092:, an analog without the nitrogen atom
716:Isoquinoline was first isolated from
352:Key: AWJUIBRHMBBTKR-UHFFFAOYSA-N
169:
149:
7:
1208:(Vol. 5). Tarrytown, NY: Elsevier.
956:vasodilators, a well-known example,
674:of pyridine, isoquinoline is a weak
362:Key: AWJUIBRHMBBTKR-UHFFFAOYAX
262:
1195:(2nd ed.). Oxford, UK: Elsevier.
1193:Handbook of Heterocyclic Chemistry
14:
1152:, Academic Press, New York, 1955.
925:antihypertension agents, such as
861:-norcoclaurine synthase, the two
588:. Isoquinoline and quinoline are
1086:(1998), an isoquinoline alkaloid
963:
947:
916:
871:4-(2-aminoethyl)benzene-1,2-diol
801:
782:
757:
533:
416:
410:
24:
936:antiretroviral agents, such as
688:of 5.14. It protonates to form
663:. It is also soluble in dilute
529:(at 25 °C , 100 kPa).
1247:, vol.5, no. 9, pages 305â312.
1115:The Royal Society of Chemistry
913:is one example (shown below).
667:as the protonated derivative.
643:in water but dissolve well in
404:
1:
769:BischlerâNapieralski reaction
631:Isoquinoline is a colorless
1366:10.1007/978-1-4612-2000-8_1
1123:10.1039/9781849733069-FP001
1018:(1-methyl-4-phenyl-1,2,3,6-
901:Applications of derivatives
867:4-hydroxyphenylacetaldehyde
33:
1443:
722:fractional crystallization
592:, which are composed of a
1174:Harris, J.; Pope, W.J. "
1161:Gilchrist, T.L. (1997).
730:PomeranzâFritsch reaction
523:
391:
371:
336:
89:
79:
67:
62:
32:
23:
1060:liquidâliquid extraction
795:PictetâSpengler reaction
696:, such as HCl. It forms
52:C=black, H=white, N=blue
42:C=black, H=white, N=blue
1400:EncyclopĂŠdia Britannica
1054:. It is also used as a
833:-norcoclaurine synthase
509:Magnetic susceptibility
1163:Heterocyclic Chemistry
1028:tetrahydroisoquinoline
1014:. A neurotoxin called
994:chain, containing two
980:
894:
818:tetrahydroisoquinoline
53:
43:
1422:Simple aromatic rings
1117:. 2014. p. 212.
979:
856:
383:C1(C=NC=C2)=C2C=CC=C1
51:
41:
1265:. pp. 490â491.
1024:dopaminergic neurons
940:with an isoquinolyl
791:PictetâGams reaction
777:phosphorus pentoxide
692:upon treatment with
606:1-Benzylisoquinoline
69:Preferred IUPAC name
1008:Parkinson's disease
822:dihydroisoquinoline
773:phosphoryl chloride
659:, and other common
431: g·mol
20:
1178:Quinoline and the
1020:tetrahydropyridine
981:
895:
873:, whereas its two
556:Infobox references
54:
44:
18:
1394:"Quinoline"
1375:978-1-4612-7375-2
1360:. pp. 3â23.
1335:10.1021/ja039712q
1329:(16): 5030â5031.
1132:978-0-85404-182-4
1003:In the human body
944:, (shown below).
582:structural isomer
564:Chemical compound
562:
561:
305:CompTox Dashboard
131:Interactive image
58:
57:
1434:
1404:
1396:
1380:
1379:
1353:
1347:
1346:
1314:
1308:
1307:
1292:(5th ed.).
1283:
1277:
1276:
1261:(5th ed.).
1254:
1248:
1237:
1231:
1224:
1218:
1215:
1209:
1202:
1196:
1189:
1183:
1172:
1166:
1159:
1153:
1146:
1137:
1136:
1107:
967:
951:
942:functional group
920:
810:phenylethylamine
805:
786:
761:
661:organic solvents
657:carbon disulfide
596:ring fused to a
578:organic compound
546:
540:
537:
536:
518:
501:
497:
452:
430:
418:
412:
406:
399:Chemical formula
329:
328:
313:
311:
295:
275:
264:
243:
235:
224:
213:
193:
173:
153:
133:
109:
34:
28:
21:
1442:
1441:
1437:
1436:
1435:
1433:
1432:
1431:
1407:
1406:
1391:
1389:
1384:
1383:
1376:
1355:
1354:
1350:
1316:
1315:
1311:
1304:
1296:. p. 492.
1285:
1284:
1280:
1273:
1256:
1255:
1251:
1238:
1234:
1228:The Merck Index
1225:
1221:
1216:
1212:
1203:
1199:
1190:
1186:
1173:
1169:
1160:
1156:
1147:
1140:
1133:
1109:
1108:
1104:
1099:
1080:
1036:
1005:
960:, shown below.
903:
890:
820:instead of the
714:
707:
685:
637:unpleasant odor
629:
565:
558:
553:
552:
551: ?)
542:
538:
534:
530:
516:
512:
499:
495:
494:
487:
450:
428:
415:
409:
401:
387:
384:
379:
378:
367:
364:
363:
360:
354:
353:
350:
344:
343:
332:
314:
307:
298:
278:
265:
253:
216:
196:
176:
156:
136:
123:
112:
99:
85:
83:
75:
74:
12:
11:
5:
1440:
1438:
1430:
1429:
1424:
1419:
1409:
1408:
1388:
1387:External links
1385:
1382:
1381:
1374:
1348:
1309:
1302:
1278:
1271:
1249:
1232:
1219:
1210:
1197:
1184:
1167:
1154:
1138:
1131:
1101:
1100:
1098:
1095:
1094:
1093:
1087:
1079:
1076:
1035:
1032:
1004:
1001:
1000:
999:
984:
983:
982:
970:
969:
968:
954:
953:
952:
934:
923:
922:
921:
902:
899:
888:
713:
710:
705:
683:
628:
625:
590:benzopyridines
563:
560:
559:
554:
532:
531:
527:standard state
524:
521:
520:
513:
507:
504:
503:
492:
489:
485:
475:
474:
471:
465:
464:
461:
455:
454:
447:
441:
440:
437:
433:
432:
426:
420:
419:
413:
407:
402:
397:
394:
393:
389:
388:
386:
385:
382:
374:
373:
372:
369:
368:
366:
365:
361:
358:
357:
355:
351:
348:
347:
339:
338:
337:
334:
333:
331:
330:
317:
315:
303:
300:
299:
297:
296:
288:
286:
280:
279:
277:
276:
268:
266:
258:
255:
254:
252:
251:
247:
245:
237:
236:
226:
218:
217:
215:
214:
206:
204:
198:
197:
195:
194:
186:
184:
178:
177:
175:
174:
166:
164:
158:
157:
155:
154:
146:
144:
138:
137:
135:
134:
126:
124:
117:
114:
113:
111:
110:
102:
100:
95:
92:
91:
87:
86:
81:
77:
76:
72:
71:
65:
64:
60:
59:
56:
55:
45:
30:
29:
13:
10:
9:
6:
4:
3:
2:
1439:
1428:
1425:
1423:
1420:
1418:
1417:Isoquinolines
1415:
1414:
1412:
1405:
1402:
1401:
1395:
1386:
1377:
1371:
1367:
1363:
1359:
1352:
1349:
1344:
1340:
1336:
1332:
1328:
1324:
1320:
1313:
1310:
1305:
1303:9783319039794
1299:
1295:
1291:
1290:
1282:
1279:
1274:
1272:9783319039794
1268:
1264:
1260:
1253:
1250:
1246:
1242:
1236:
1233:
1229:
1223:
1220:
1214:
1211:
1207:
1201:
1198:
1194:
1188:
1185:
1181:
1177:
1171:
1168:
1164:
1158:
1155:
1151:
1145:
1143:
1139:
1134:
1128:
1124:
1120:
1116:
1113:. Cambridge:
1112:
1106:
1103:
1096:
1091:
1088:
1085:
1082:
1081:
1077:
1075:
1073:
1069:
1065:
1061:
1057:
1053:
1049:
1045:
1041:
1033:
1031:
1029:
1025:
1021:
1017:
1013:
1009:
1002:
997:
993:
989:
985:
978:
974:
973:
971:
966:
962:
961:
959:
955:
950:
946:
945:
943:
939:
935:
932:
928:
924:
919:
915:
914:
912:
911:dimethisoquin
909:anesthetics;
908:
907:
906:
900:
898:
892:
884:
883:norcoclaurine
880:
876:
872:
868:
864:
860:
855:
851:
849:
845:
841:
838:
834:
832:
827:
823:
819:
815:
811:
806:
804:
799:
796:
792:
787:
785:
780:
778:
774:
770:
765:
762:
760:
755:
753:
750:
746:
742:
739:
735:
731:
726:
723:
719:
711:
709:
703:
699:
695:
691:
687:
686:
677:
673:
668:
666:
662:
658:
654:
653:diethyl ether
650:
646:
642:
638:
634:
626:
624:
622:
619:
615:
611:
607:
603:
599:
595:
591:
587:
583:
579:
576:
573:
569:
557:
550:
545:
528:
522:
514:
510:
506:
505:
490:
484:
480:
477:
476:
472:
470:
469:Boiling point
467:
466:
462:
460:
459:Melting point
457:
456:
448:
446:
443:
442:
438:
435:
434:
427:
425:
422:
421:
403:
400:
396:
395:
390:
381:
377:
370:
356:
346:
342:
335:
327:
323:
322:DTXSID2047644
319:
318:
316:
306:
302:
301:
294:
290:
289:
287:
285:
282:
281:
274:
270:
269:
267:
261:
257:
256:
249:
248:
246:
244:
239:
238:
234:
230:
227:
225:
223:ECHA InfoCard
220:
219:
212:
208:
207:
205:
203:
200:
199:
192:
188:
187:
185:
183:
180:
179:
172:
168:
167:
165:
163:
160:
159:
152:
148:
147:
145:
143:
140:
139:
132:
128:
127:
125:
121:
116:
115:
108:
104:
103:
101:
98:
94:
93:
88:
82:Benzopyridine
78:
70:
66:
61:
50:
46:
40:
36:
35:
31:
27:
22:
19:Isoquinoline
16:
1398:
1390:
1357:
1351:
1326:
1322:
1312:
1288:
1281:
1258:
1252:
1244:
1240:
1235:
1227:
1222:
1213:
1205:
1200:
1192:
1187:
1179:
1175:
1170:
1162:
1157:
1149:
1110:
1105:
1048:insecticides
1037:
1006:
988:tubocurarine
931:debrisoquine
904:
896:
878:
858:
830:
807:
800:
788:
781:
766:
763:
756:
734:benzaldehyde
727:
715:
704:, such as BF
694:strong acids
681:
669:
630:
572:heterocyclic
568:Isoquinoline
567:
566:
482:
90:Identifiers
80:Other names
73:Isoquinoline
15:
1090:Naphthalene
1074:inhibitor.
1070:, and as a
1012:neurotoxins
745:benzylamine
702:Lewis acids
633:hygroscopic
602:derivatives
436:Appearance
392:Properties
229:100.003.947
171:ChEMBL12315
151:CHEBI:16092
84:2-benzazine
1411:Categories
1097:References
1052:fungicides
1034:Other uses
958:papaverine
938:saquinavir
863:substrates
826:enzymology
712:Production
641:solubility
627:Properties
618:amino acid
614:papaverine
424:Molar mass
293:JGX76Y85M6
182:ChemSpider
118:3D model (
97:CAS Number
1343:0002-7863
1084:Eletefine
1072:corrosion
998:linkages.
927:quinapril
848:catalyzes
678:, with a
670:Being an
610:alkaloids
586:quinoline
250:204-341-8
242:EC Number
1294:Springer
1263:Springer
1078:See also
1068:terpenes
1058:for the
875:products
842:) is an
840:4.2.1.78
814:aldehyde
793:and the
718:coal tar
621:tyrosine
612:such as
598:pyridine
575:aromatic
515:â83.9·10
511:(χ)
202:DrugBank
107:119-65-3
1056:solvent
812:and an
767:In the
749:glyoxal
698:adducts
649:acetone
645:ethanol
594:benzene
549:what is
547: (
519:cm/mol
479:Acidity
445:Density
429:129.162
260:PubChem
211:DB04329
1372:
1341:
1300:
1269:
1129:
1064:resins
1044:paints
992:carbon
844:enzyme
828:, the
752:acetal
747:and a
741:medium
672:analog
544:verify
541:
517:
500:
496:
451:
376:SMILES
162:ChEMBL
63:Names
996:ester
846:that
824:. In
700:with
690:salts
665:acids
502:5.14
453:g/cm
449:1.099
341:InChI
142:ChEBI
120:JSmol
1370:ISBN
1339:ISSN
1298:ISBN
1267:ISBN
1127:ISBN
1066:and
1050:and
1040:dyes
1016:MPTP
929:and
885:and
877:are
869:and
865:are
789:The
738:acid
676:base
284:UNII
273:8405
191:8098
1362:doi
1331:doi
1327:126
1180:iso
1176:iso
1119:doi
1062:of
879:(S)
859:(S)
831:(S)
775:or
584:of
310:EPA
263:CID
1413::
1397:.
1368:.
1337:.
1325:.
1321:.
1141:^
1125:.
1046:,
1042:,
837:EC
708:.
655:,
651:,
647:,
623:.
604:.
493:BH
491:pK
488:)
481:(p
1378:.
1364::
1345:.
1333::
1306:.
1275:.
1135:.
1121::
893:.
891:O
889:2
887:H
881:-
835:(
706:3
684:a
682:K
680:p
539:N
498:=
486:a
483:K
417:N
414:7
411:H
408:9
405:C
312:)
308:(
122:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
